


Nobody's Perfect

by FriendofCarlotta



Category: Supernatural
Genre: Alternate Universe - 1920s, Arranged Marriage, Blow Jobs, But no Boys in Dresses Sorry, Castiel and Dean Winchester in Love, Explicit Sexual Content, First Kiss, Gangsters, Happy Ending, Love Confessions, M/M, Masturbation, Minor Angst, Minor Charlie Bradbury/Dorothy Baum, Minor Dean Winchester/Abaddon, Minor Gabriel/Abaddon, Misunderstandings, Mob Violence, Pining, Some Like It Hot AU, gender bending, period slang, screwball comedy
Language: English
Status: Completed
Published: 2020-12-01
Updated: 2020-12-18
Packaged: 2021-03-09 21:55:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 36,515
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27823360
Author URL: https://archiveofourown.org/users/FriendofCarlotta/pseuds/FriendofCarlotta
Summary: Chicago, 1929: Penniless musicians Cas and Gabe are having a rough go of it. First, they narrowly escape a police raid on a speakeasy, then they accidentally witness a gangland murder committed by the notorious “Spats” Crowley.To get away from Crowley, Cas and Gabe join a band heading to a three-week engagement at a fancy Florida resort. The band’s lead singer is one Dean Winchester, who’s looking to solve his family’s financial difficulties by getting engaged to a wealthy heiress.That plan hits a snag when Dean finds himself falling for his tousle-haired, blue-eyed band mate instead. With one on the run from a gangster and the other determined to strike it rich, will Cas and Dean get a chance to follow their hearts?
Relationships: Castiel/Dean Winchester
Comments: 96
Kudos: 95
Collections: The Destiel Fan Survey Favs Collection





	1. Chapter 1

**Author's Note:**

> Some Like It Hot is one of my all-time favorite movies - not just because it's incredibly funny, but also because of how truly, astonishingly gay it is for a movie made in the 1950s. But everything is better with Dean and Cas, right? So here we are.
> 
> I did a ton of research to try to make sure the period details (language, clothing, amenities, music, etc.) are accurate, but I'm not a 1920s expert by any means. If you happen to be one, I hope you'll forgive me for anything that might've slipped past me.
> 
> In several big American cities, the 1920s were a period when gay culture and gender-bending performers briefly flourished, before the Depression era brought a crackdown. The [first gay rights organization](http://chicagolgbthalloffame.org/gerber-henry) in the U.S. was actually founded in Chicago in 1924!
> 
> That said, homosexuality was still frowned upon outside of certain accepting venues and neighborhoods, so the way Dean and Cas interact in this fic (at least when they're out in public) is going to reflect that. 
> 
> Historical details aside, this is supposed to be a bit of silly fun at a time when I figured this fandom could use a bit of silly fun. So above all, I hope this makes you laugh.
> 
> As always, a HUGE, ginormous thank you to [tiamatv](https://archiveofourown.org/users/tiamatv/pseuds/tiamatv) for her thoughtful, supportive beta work and general wonderfulness. You make my words so much better! Thank you also to my lovely friends [dothraki_shieldmaiden](https://archiveofourown.org/users/dothraki_shieldmaiden/pseuds/dothraki_shieldmaiden) and [duckyboos](https://archiveofourown.org/users/Duckyboos/pseuds/Duckyboos) for their cheerleading. This fic would not exist without you three.
> 
> I have almost the whole thing written, so you can expect weekly updates!
> 
> Enjoy :) .

**Prologue**

_Chicago, 1929: The Age of Prohibition_

At twenty minutes to midnight, traffic is sparse on the city streets. A Packard Twin 6 Roadster rattles past, splashing a lonely pedestrian with detritus from the puddles gathering on the wet asphalt. The pedestrian turns up his collar, hunches his neck and hurries onward.

Anyone out in the streets at this hour would prefer not to be seen. Well-intentioned people, good family men, have no business being out on the town at a time like this. They should be in bed, kissing their wives goodnight, perhaps listening to a last song on the wireless before they turn in.

Those people don’t know, or choose to ignore, the other life that goes on behind the scenes of a Chicago night.

At King’s Funeral Parlor, the green neon sign advertising “24-hour service” crackles on and off with a disagreeable buzz.

A visitor with urgent undertaking needs at this ungodly hour would find himself ushered by a small man in a tailcoat and horn-rimmed glasses into a warm sitting room, with comfortably upholstered chairs and large floral arrangements. Perhaps the visitor would wonder why a second man, seated at a small table in the back of the room, doesn’t so much as offer a greeting. Or why the sound of fast-paced jazz emanates faintly from beyond the wall at the man’s back.

As our visitor leaves, he might pass by the delivery entrance, where a hearse is just now pulling up and disgorging two men who carry between them a heavy, gleaming mahogany coffin. This coffin, it should be said, does not contain the remains of a departed relative. Instead, the coffin’s occupants slosh and clink against each other, emitting, even through the wood, a faint odor of rye and juniper.

The pallbearers slouch off, staggering under their burden, even as another, smaller man hops off the back of the hearse. His coat is of soft, black wool and elegantly cut, the cuffs of his pinstriped slacks carefully tailored to the exact length that is currently fashionable. The spats that cover his instep and ankle gleam a dazzling white, somehow unaffected by the wetness of the rain, or the grime of the Chicago streets. Despite his small, stocky frame, the man’s posture speaks of the easy confidence of the rich. His name is “Spats” Crowley.

If our visitor managed to observe Spats and his companions as he passed, he wouldn’t be the only one. In the shadows thrown by the department store across the street, two other men wait.

One is federal agent Benny Lafitte, a great, burly bear of a man wearing a newsboy cap with a scuffed brim and a fishbone coat that is noticeably less ostentatious than the duds worn by Spats, who is now following the pallbearers inside the funeral establishment.

Agent Lafitte turns to the small, rat-faced individual next to him, who goes by the name of “Toothpick” Marv. “Alright, Toothpick. You sure this is the joint?”

Marv nods, transferring the eponymous wooden stick to his other cheek. “That’s the one.”

“Who runs it?”

Marv shifts uneasily from one foot to the other. “Already told you.”

“Remind me,” Benny growls, squaring his shoulders to tower over the other man.

“Spats. Spats Crowley,” Marv mutters, almost despite himself.

“Nice work, brother. Now, what’s the password to get in?”

“‘I came for grandma’s funeral,’” Marv intones. He holds out a ribbon of black crepe. “That’s your ticket inside. If you want a seat by the stage, tell them you’re one of the pallbearers.”

Lafitte nods his acknowledgement. A uniformed cop walks up from around the corner. “When do we move in, agent?”

Lafitte consults his watch. “Gimme ten minutes.”

Marv shuffles uncomfortably, watching his breath fog into a diaphanous cloud in front of him. “Look, I’d better go. If Spats catches me here, it’s ‘Goodbye, Marv.’”

Lafitte claps a heavy hand on Marv’s shoulder, one corner of his lips ticking up at the weaselly man’s flinch. “Goodbye, Marv.”

Marv turns up his collar against the chill and strides off down the street. Before long, a billow of steam rising from a grate in the pavement swallows him up.

***

**PART I**

“Hey, Gabe?”

Cas leans over to elbow his older brother, even as his fingers keep strumming away at the strings of his bass fiddle. He's playing a fast jazz tune, just one of the more than twenty musicians lined up in a semi-circle along the back of the stage. The audience’s attention is almost entirely focused on the line of ten chorus girls in front, so no one’s going to notice a quick, whispered conversation.

Gabe ignores Cas in favor of winking ostentatiously at one of the shimmying girls as she passes their corner. Cas elbows him harder, and Gabe nearly loses his grip on his saxophone. “Hey, baby bro! Watch the goods. I lose my sax, we lose our paycheck.”

“You were ignoring me,” Cas says, eyes narrowed in exasperation. “Do I need to put on a pair of tights and high heels to get your attention?”

Instead of answering right away, Gabe plays an ostentatious, lightning-fast arpeggio on his sax, in a transparent effort to show the bandleader he’s earning his keep.

At the front, the girls are switching it up, trading the shimmy of the Charleston for the exaggerated kicks and hops of the Black Bottom. In the first row, completely unaffected by the supposedly titillating sight, sits a burly man in a newsboy cap and a fishbone coat. He’s scanning the room with a sharp eye that’s an unusual trait for speakeasy patrons this time of night. Cas frowns, thoughtful.

“It’s no good, Cassie.” Gabe grins mischievously, eyes still on the girls. “Your legs aren’t nearly as shapely as Ginger’s over there.”

“I’ve had no complaints,” Cas retorts, with supreme dignity. “But what I was going to ask is, do we get paid tonight?”

Gabe nods vaguely, eyes now following a girl with dark hair and a mischievous twinkle in her eye. “Yeah. Why?”

“Because I lost a filling in my back tooth,” Cas answers, tonguing experimentally at the offending spot. “I need to see a dentist and get it fixed.”

Gabe pauses to gape at Cas, midway through bringing his sax to his lips for another couple of notes. “We’ve been out of work for weeks and you wanna blow our first paycheck on the _dentist_?”

Cas glares back at him. “Look, if you think you’re spending _our_ money taking out Ginger or Veronica or whoever the flavor of the week is now…”

“I would never,” Gabe exclaims, hand splayed on his chest in mock affront. “We owe two months’ back rent, our check at the laundry bounced, and we’re on the hook for fifty bucks at the delicatessen. How can you be so selfish, Cassie? The _dentist_. Seriously.”

Cas winces in acknowledgement of Gabe’s point. “Fine. Tomorrow, we’ll start paying down each of those accounts.”

“No, we won’t,” Gabe says, before he rattles off another fast couple of notes to impress a blonde hopping past him in her rhinestone-embroidered one-piece.

“We won’t?”

Gabe digs in the inner pocket of his suit jacket for a badly creased booklet that turns out to be a racing form. “Tomorrow, we’re going to the dog track and putting the whole bundle on Greased Lightning.”

Now it’s Cas’ turn to gape. “You want to spend our entire paycheck on… a dog.”

“Not just any dog, Cassie.” Gabe points down at the listings. “A dog with ten-to-one odds! We could make a killing!”

“What you mean is, we could _be_ killed, by our creditors,” Cas grumbles absently, his eyes falling once again on the burly man in the front row. The man is reaching into the inside pocket of his coat for something, a look of intense concentration on his face. The hair on Cas’ forearms rises with his sudden unease.

“Don’t know what you’re so worried about, baby bro,” Gabe says easily. “We’ve got a good thing going here. This job’s going to last a long time.”

“What if the police raid the place?” Cas answers, trying to focus his gaze on the gleaming object in the man’s hand.

Gabe scoffs. “Why d’you always have to be such a worrywart?” In an annoyingly accurate imitation of Cas’ voice, he rumbles, “What if the police raid the place? What if Lake Michigan overflows? What if the stock market crashes?”

The man is now busy pinning the gleaming object to the front of his coat. It’s a badge.

“Gabe.” Cas is a little proud of how steady he sounds as he nudges his brother and points at the front row. “The police are raiding the place.”

To Gabe’s credit, when action is called for, he doesn’t hesitate. In one smooth motion, he packs up his sax and grabs his coat. “Fuck. Let’s get out of here while the getting is good.”

Cas stows his bass in its case as unobtrusively as possible — a literal tall order with a six-foot instrument — and sneaks after Gabe. They’re almost to the back of the room when the sound of axes breaking through wood starts up at the front.

“Chicago PD! This is a raid!”

The crowd descends into chaos with staggering speed, people screaming and flailing and jostling each other to find an exit not barred by a guy in uniform. Cas feels Gabe’s elbow nudge him. “The fire stairs! C’mon.”

They change course slightly, avoiding the back door and heading for the storage room instead. Sure enough, when they get inside, there’s no one else there, and the window opens onto a rickety metal fire escape. Cas decides not to think about why his brother already knew the quickest route out of the place, and to be grateful instead.

The window sticks a little, but they shimmy through the narrow gap they’ve managed to create, Cas’ bass fiddle almost getting stuck along the way. It’s an awkward climb down with two instrument boxes, but they manage it between them, and when they land in a puddle halfway down a dark alley, the policeman watching that side of the building pays them no mind.

In fact, he has his back turned, busy talking to a man in a luxurious black coat and a gleaming pair of spats. In passing, Cas hears the cop say “Toothpick Marv.” But Gabe pulls him along, and soon they’re out of the alley and in the comparatively bright environs of the sidewalk in front of King’s Funeral Parlor. A furious group of squirming, cursing line girls is being crowded into a squad car by a small handful of overwhelmed-looking uniforms. Cas and Gabe head the other way, blending into the small crowd that’s gathered on the sidewalk to watch the commotion.

“Whoever Toothpick Marv is, he better watch his back,” Gabe mutters. “That guy was Spats Crowley. He owns the joint.”

Shoulders slumping, Cas blows out a heavy breath through his nose. “Well, it doesn’t look as though we’re getting paid tonight. At least we don’t have to worry about which bill to settle first anymore.”

***

“Son of a bitch!” Dean wiggles out from under the cast-iron radiator, wiping at his wet face with the back of his hand. “The damn thing leaked on me.”

From the other side of the small living room, Mary snorts. “That radiator’s got it in for you, son. It never does this to _me_.” She swipes a hand towel off the stack of newly folded ones on the ironing board and passes it to her son. “You know, I might point out that I didn’t _ask_ you to fix the radiator. I’m perfectly capable of grabbing a wrench and closing up a leaking valve.”

Dean shrugs, rubbing at the rust-colored liquid on his forehead. “Yeah, but I’m here for once, so I wanna take care of you.” He looks down and fidgets with the towel in his hands. 

On paper, his ma’s slightly rundown fifth-floor shoebox is his home too. But he’s on the road so much, traveling with whatever band will take him on, that he’s hardly ever around. His latest touring engagement ended just three nights ago. 

He doesn’t like to think about what his ma does with herself in the meantime, with no one to keep her company but her memories and a surly landlord who’s threatened to kick her out three times in the past year. Clenching his hands around the towel, Dean rubs at his face again, a little harder, until the skin on his forehead stings. “Also, wanna make sure you don’t have to waste money on a handyman when I’m not around,” he adds.

“I’m not some damsel in distress,” Mary says, rolling her eyes at her first-born. “You’ve got paychecks coming in more or less regular, I can always pick up more hours at the cannery, and I’ve got my widow’s pension.” She jerks her chin at the side table beside the chintz-upholstered couch, where the picture of the late Captain John Winchester, fallen on the Western Front in 1917, sits in pride of place. “Might be late on the rent sometimes, but between the two of us, we always do scrape it together in the end.”

Dean doesn't answer. They both know the cannery doesn’t have any more hours to give, and the widow’s pension is a drop in the bucket at best. They’ve had this talk plenty of times, so what’s the use of having it again?

Instead, he loses a moment or two looking at the picture of his father, stern gaze under bushy black brows. He’s got a few good memories of John Winchester, but they’re buried under years of watching his ma go hungry because his father left most of his factory wages at the bottom of a bottle again. Mary would always make sure her boys had enough, although, unbeknownst to her, Dean sometimes squirreled away his own portion for Sammy, just to make extra-sure he had a full belly.

Of course, Sammy is now Samuel Winchester, Esq., a married man and small-town lawyer two states over. Dean knows Sam’s offered to send back money to help out, but Mary won’t let him because “the boy has a growing family to take care of,” and in any case, Dean doesn’t need his little brother keeping him fed and clothed. He’s got a good face that people like to see on stage, and a good voice they like to hear, and for now, that’s enough. 

Rolling his shoulders to shake those unpleasant thoughts off his back, he saunters over to the gas stove and peeks into the pot bubbling away there. Mary slaps his hand away. “Hold your horses, son. It’s not ready.”

Dean squints suspiciously at her. “What… is it?”

“Never you mind.” Mary crowds him away from the stove with a shove of the hip. “Just this once, would you let me cook for you without watching me like a hawk?”

“No. Because the last time I let you cook for me, you damn near set the whole building on fire.”

Mary glares at him, but they both know it’s true. Mary Winchester is not an accomplished cook. More often than not, growing up, Dean was the one who boiled or fried whatever meager canned goods and meat scraps they managed to afford.

“How’d it go at the artists’ agencies this morning? You find a new job?” Mary asks, pretending not to notice the way Dean is crowding into her space, pushing her away from the stove in a battle of inches.

Dean shrugs. “The Singer agency’s got something in Florida. Three-week engagement at some fancy resort, with Donna’s band. Not sure I should take it though.” 

Mary studies him closely, reading his mind in the way only she can. “The agency covering travel expenses?”

Dean grunts vaguely, because he can’t deny that travel expenses are indeed covered. Mary plants both hands on her hips. Despite the loose fit of her house dress and the mystery stain on the front of her apron, she manages to look imposing. “Why on earth wouldn’t you go then?”

“Don’t wanna leave you all by yourself again so soon,” Dean mumbles, lifting up the pot lid and stirring the brownish liquid inside. “Hey, how ‘bout I stop by the delicatessen for some ham and potato salad?”

Ignoring the obvious deflection, Mary pokes at her son’s shin with a nylon-clad toe. “How ‘bout you go on that trip to Florida and stop hanging off your mother’s skirt?” Dean picks up a wooden spoon and takes a taste of the contents of the pot, wincing a little. The food is somehow both too salty and lacking in flavor. He still can’t tell what it actually _is_ either.

“Besides,” Mary continues, unmoved, “some fancy resort in Florida? There’s bound to be all kinds of beautiful heiresses swanning about, just waiting for a handsome Chicago boy to sweep them off their feet.” She grins wickedly. “Get one of ‘em to marry you, so I can live in the style to which I’m planning to become accustomed.”

Dean looks back at her, considering. He knows she’s joking, but something about what she’s saying has set the cogs in his brain to turning.

“Y’know, that’s not a half-bad idea?” he says, winking ostentatiously, like he’s still kidding around and not halfway resolved to a plan already. “I guess I _could_ be persuaded to show the ladies down there a good time. Wouldn’t hate to be some rich woman’s husband. Wear all the best suits, drink all the best whiskey, never fix another leaky radiator. Buy you a beachside mansion.”

Mary frowns, hands on her hips again. “I ought to know better than to run my mouth around you. You just take that trip, but don’t be hatching any harebrained schemes, you hear? Like I said, we get by just fine.”

In lieu of an answer, Dean gathers his mother’s hand in his own and sweeps her around the cramped apartment in an impromptu waltz. Mary swats at him, but she lets herself be twirled until they both collapse, laughing, onto the couch.

Dean looks over at his mother, and one corner of his lips quirks up in a teasing grin as visions of a life of luxury dance in his head like sugar plums. “What d’you say we turn off the heat on that abomination, and treat ourselves to a couple of hot dogs?”

*** 

Cas hunches his shoulders against the icy breeze coming off the lake. “I still think we should have taken that Florida engagement Singer’s agency was offering.”

Gabe huffs out a put-upon sigh as he hurries along the sidewalk, sax case swinging at his side. “Please. That’s horsefeathers, Cas. You know who plays in bands at fancy resorts in freaking Florida?”

Cas shrugs, as much as he’s able while carrying his bass and trying to conserve maximum body heat under his thin overcoat. “People who get paid?”

“Past-their-prime geezers who can’t cut it in the city anymore, that’s who,” Gabe declares confidently. “Now where did Kali say it was…”

Kali, Gabe’s on-again-off-again girlfriend, is an Indian diplomat’s daughter, and therefore owns a car of her own. She’s stored it at a public garage for the night to keep her parents from finding out she’s letting someone as disreputable as Gabe borrow it.

“There!” Gabe points halfway down the block at a gloomy driveway set into the first floor of an office building. Their goal now in sight, Cas and Gabe quicken their steps, trying to get to any kind of space that will offer even a slight bit of shelter from the wind, and from the driving snow that’s now started up.

“I still can’t believe you want to drive to Urbana in this weather. It’s hours away!” Cas grits out between chattering teeth as they walk down the driveway into the garage’s interior.

“You wanted a paycheck. There’s a paycheck in Urbana,” Gabe says evenly as he approaches the attendant’s desk.

“Yes, for one night!” Cas points out, reasonably, he thinks. “There’s no snow in Florida, _and_ it would’ve been guaranteed work for three weeks.”

“God, will you shut up about Florida already?” Gabe turns to the attendant and dangles a set of keys. “The green coupe over there.”

In the back of the garage, a poker game is in full swing. Six men are grouped around the table, a pile of chips and a heaping-full ashtray between them. One of the men is shifting a toothpick back and forth between his cheeks.

“You want her filled up?” the attendant growls.

Cas gives a tight smile as he considers the meager contents of his pockets. “Forty cents’ worth, please.”

Gabe elbows him, then turns to the attendant. “This is on Ms. Patel’s account, right?”

The attendant nods curtly, and Gabe waves a generous hand in the direction of the coupe. “Fill ‘er up then.”

Cas side-eyes his brother as they stroll over to the car. “You’re a real gentleman. I don’t know why Kali hasn’t proposed to you yet.”

“Eh.” Gabe shrugs easily, a teasing gleam in his eye. “She knows I’m no good, but she likes me anyway.”

As the attendant removes the fuel nozzle from the gas pump and inserts it into the coupe’s tank, the sound of screeching tires draws everyone’s attention to the open garage gate.

A brand-new Hudson 7 Roadster with a leather top pulls up and disgorges four men, each holding a Tommy submachine gun. Cas’ brain supplies that these guns are also known as “Chicago typewriters,” because from a distance, their rapid rate of fire resembles the sound of typewriter keys. 

At a distance is very much where Cas wishes to be at the moment. His brain is great at useless facts, but not so great at dealing with stressful situations. 

Luckily, Gabe is better at those, because he pulls Cas down into the space between the coupe and the car next to it, out of sight of the newcomers. The attendant is frozen, still holding the fuel nozzle. The poker players have shot out of their seats, hands in the air.

Another man steps out of the Roadster. Cas doesn’t need Gabe’s shocked intake of breath to recognize him: Spats Crowley. Slow and measured, Spats steps up next to his men, who have formed a single line, guns pointed at the poker players.

“All o’ you, up against that wall,” one of the armed men growls, jerking his chin at the brick barrier behind the table. The players comply, albeit slowly.

From where he’s crouching behind the coupe, Cas can make out half of Spats Crowley’s face, smiling beatifically at the players now lined up against the brick. “Well, hello there, Marv. Long time no see.”

Toothpick guy turns his head, keeping both hands firmly planted on the wall. “What’s all this, Spats?” Cas thinks Marv is trying to sound casual, but he’s missed it by a mile.

“Just came to thank you, Marv,” Crowley says evenly, walking toward the table to pick up the deck from the abandoned poker game. He shuffles it with careful deliberation, then studies the topmost card.

“You don’t have to thank me, Spats,” Marv squeaks, and even from all the way across the garage, Cas can practically count the beads of sweat forming on the man’s forehead. 

“That’s not what _I_ heard, Marv,” Crowley says, an edge of menace creeping into his quiet voice now. “I heard you recommended my funeral parlor to some friends of yours at the Chicago PD.”

“Wasn’t me, Spats, honest!” If Cas thought Marv’s voice had reached a squeaky register before, it’s nothing compared to the high-pitched panic lacing it now.

Crowley shakes his head sadly, like he’s genuinely disappointed, then starts shuffling the cards again. “Goodbye, Marv,” he tells the deck. The sound of gunfire fills the cavernous space. 

Up close, Cas’ shell-shocked brain notes absently, it’s nothing like typewriters at all.

When the sound stops, six men lie dead on the floor. Cas is holding his breath, and next to him, he thinks Gabe is too.

_Clank!_

The attendant has dropped the fuel pump, the jangle of metal on concrete ludicrously noisy in the literal dead silence of the garage.

Someone lets out a startled squeak. Cas would like to think it was Gabe, but he can’t be sure.

The gangsters spin around as one.

“Alright,” Crowley snarls. “Come on out of there.”

Cas knows it’s no good, so he rises slowly from his crouch on the floor, Gabe right behind him.

“We… didn’t see anything,” Gabe croaks. “And even if we did… we wouldn’t care, right?”

Gabe turns to Cas, who, despite his extreme terror, feels the distinct urge to roll his eyes at his brother. He can’t seriously think this is going to work. 

Distantly, Cas wishes he’d thought to make a will. Scratch that. He wishes he had anything to leave someone in a will. Or, really, anyone besides Gabe to _name_ in a will. God, his life is nothing to write home about these days. Maybe he can convince Spats and his men that he’s too pathetic to kill.

Meanwhile, Gabe is still rambling on. “We’re… nothing but a couple of musicians. Came in to pick up a car. So we’ll just…” He points at the sidewalk outside, then tugs on the sleeve of Cas’ coat. “C’mon, Cas.”

“Where do you think you’re going?” There it is again, that edge of menace. “I’m not in the habit of leaving witnesses.”

In the corner of his eye, Cas sees one of the dead men move. Perhaps this one’s not so dead after all. The man, Marv, rises slowly, soundlessly, one bloodied hand stretching for the phone that’s sitting on a shelf halfway up the wall. Fingers inches from the machine, his leg buckles, and he knocks the thing to the floor with a clatter. The gangsters spin around to face the wall again. Spats grabs the gun of his nearest henchman and pulls the trigger, spraying bullets.

For one, two, maybe three seconds, Gabe and Cas are frozen. Then, Cas feels another tug on his sleeve, and the tickle of Gabe’s voice in his ear. “Let’s get the hell out of here.”

The words jolt Cas into motion. Gripping his bass tight, he hightails it out of the garage, running after Gabe even as the sound of shouting starts up, followed by more gunfire, this time aimed at them.

By some miracle, the sound of sirens drifts over from a few blocks away, and the gunfire stops. As he runs, Cas takes a moment to think of the poor attendant. Did he make it out? It seems unlikely.

When his lungs scream for relief, he finally slows, one hand flailing out to stop Gabe in his tracks as well. Cas ducks into the nearest alley and bends down, supporting himself on his instrument with one hand and his thigh with the other as he pants. “What… the hell… are we going… to do… now?”

“Don’t… know,” Gabe wheezes. He’s similarly bent double, trying to get air back into his tortured lungs. “But Spats… isn’t gonna… let this… go.”

As their breaths slowly return to normal, they straighten, staring helplessly at each other. “You think he’ll track us down,” Cas says.

“A matter of when, not if,” Gabe agrees.

“So what?” Cas asks desperately.

Gabe’s lips quirk up in a small grin. “So we go to Florida.”

*** 

Dean manages to arrive at the Dixie Flyer’s station platform ten minutes before departure time, which he figures should earn him some credit.

Instead, all he gets is a disapproving once-over at the compartment door from Adler, the pain-in-the-neck band manager. Adler’s patronizing scrutiny takes in the slight scuff on the toe of one of Dean’s loafers, and the stain on his tie. His raised eyebrow is probably a comment on the fact that Dean’s suit is a simple wool flannel, as opposed to Adler’s ostentatious, double-breasted Italian.

With a weary shake of the head, Adler bends over his clipboard to put a check mark next to Dean’s name, and waves for him to proceed through the sliding door.

Every time he takes an engagement with The Dapper Donna Orchestra, he conveniently forgets that Adler comes with the package. It’s a good thing Donna herself, while a stickler for rules, has a good heart and a pronounced sense of fairness that tends to balance out Adler’s petty impulses. 

Dean scowls as he casts around for a place to sit in the carriage. There’s more than a dozen people already here, and some familiar faces shoot him a grin or a wave, which Dean returns half-heartedly. His mood picks up some when he spots his best friend, trombonist Celeste “Charlie” Bradbury, on one of the benches near the back of the compartment.

“Charles,” Dean says, jerking his chin at the petite redhead as he slumps into the bench in front of hers. He deposits his suitcase and instrument case unceremoniously on the floor next to him. “Didn’t know _you_ were in on this jaunt.”

Charlie bounces up from her seat with the enthusiasm of a sugar-addled toddler and wraps her arms around Dean from behind, mussing up her fashionably cut bob against his stubbled cheek. Dean got a bit of a late start this morning, so his shave wasn’t as thorough as it might’ve been.

“We haven’t even left the station, and you’re already a wet blanket,” Charlie pouts and squeezes him harder than should be possible for someone that small in size.

“Yeah, well,” Dean grumbles, but he leans into the hug a little, “you would be too if you’d gotten the Adler eyeball this early in the morning.”

Charlie snorts and finally relinquishes her death grip on Dean’s neck, bouncing back against her seat. Dean shifts so he’s leaning against the window and stretches his legs as best he can along the length of the bench. The window feels icy even through the fabric of his suit, but it’s either that or getting a crick in the neck from turning around to talk to Charlie every few seconds.

“Please,” Charlie snorts. “Not only did I get the eyeball, but the first thing he said to me was, ‘Young lady, I do not approve of this newfangled fashion of putting women in men’s trousers.’” She wiggles one of her legs, which is indeed encased in a pair of high-waisted tan slacks. “If I’d been wearing one of my ties, he probably would’ve had an apoplexy.” She puts a thoughtful finger to her coral-red lips. “Maybe I should put one on now. Plenty of hours left in the day.”

Dean snorts. “What’s a bluenose like him doing managing _this_ band anyway? Donna’s signature move is wearing a man’s suit during performances. That’s _why_ she’s Dapper Donna.”

“I’ve got a funny feeling his morals are flexible when there’s money to be made,” Charlie says, shrugging.

Dean grunts his agreement just as the sound of fussy throat-clearing reaches him from the other end of the carriage. It’s Adler, of-fucking-course.

“Welcome,” Adler says, unctuously, “one and all. Before we set off, let me make one thing perfectly clear.” He pauses for dramatic effect. “There is to be _no funny business_ on this trip.”

Dean very pointedly doesn’t look at Charlie, who is _definitely_ making rude hand gestures at Adler from behind Dean’s seat.

“That includes,” Adler creases his eyebrows into a stern V, “the consumption of alcohol.”

His eyes zero in on Dean immediately, and Dean shifts self-consciously to hide the telltale bulge of the flask in the inside pocket of his suit jacket.

When Adler finally moves on, Dean’s feeling more disgruntled about this trip than ever. To distract himself from his foul mood, he looks around the carriage at the other players. There’s Garth, Lee, and also Dorothy, a girl Charlie’s had a crush on for years. There are quite a few new faces, too, including… _hello_. A slim but solidly built guy with messy dark hair and a sharp jaw, who’s perching stiffly on one of the benches near the front of the carriage. It’s kind of a shame Dean’s never met him before, because he’s _very_ easy on the eyes. Speaking of eyes, those baby blues he’s got turned on Adler like a good little schoolboy? Damn.

Dean kicks himself internally. Any other time, he would’ve tried for something with a face that nice, but the conversation with his ma has been on his mind. If he really could find himself a beautiful girl with money who’d put up with him? His family’s troubles would be over. No more trudging from one agency to the next, looking for that next engagement, no more worrying about the future. No more landlords threatening to kick them to the curb.

Besides, what are the chances Blue Eyes is even interested in keeping company with a man? If he were, they probably would’ve run into each other at least a time or two, playing the South Side drag balls.

That thought makes Dean gloomy again, but as he reluctantly tears his eyes away from Blue Eyes’ five o’clock shadow, a somewhat cheering idea occurs to him. Most Pullman train cars have a small smoking room attached to the men’s room, and the car hired by the Singer Agency to ferry Dapper Donna and her orchestra to Florida is probably no exception. What better place to retreat with his flask and regret his life choices?

As soon as Adler wraps up his sanctimonious speech (“there will be no violations of curfew,” “I will not abide hanky panky between members of the band,” etc. etc.), followed by a much more agreeable one from Donna, Dean slinks off.

Safely ensconced inside the smoking room, Dean stretches out, one leg propped on the upholstery. Maybe he should roll a cigarette just to keep up appearances, but he’s really more of a social smoker, and his large fingers make rolling the fragile papers a frustrating business.

So instead, Dean reaches into his jacket pocket and pulls out his contraband. The flask is one of the few things of his dad’s that came back from the front, and despite the literal and figurative blows his father dealt him, Dean treasures it as a keepsake.

He puts the flask to his lips and relishes the burn, the warmth spreading down his throat and all the way to the tips of his fingers.

The door swings open, and Dean sits up so fast, he almost spills his bourbon. “Son of a bitch!”

The newcomer, Blue Eyes, freezes in the open doorway, exposing Dean’s transgression to anyone who might chance to pass through the corridor behind him. 

“Well? In or out?” Dean growls.

“Uh,” the guy says, eloquently. “I suppose it depends. Am I disturbing you?”

He looks so damn earnest, it makes Dean’s hackles come down almost all the way. “Nah, man,” Dean mumbles, shrugging. “Just thought you were Adler and got a little flustered.” He holds out the flask. “You want some?”

The guy seems on the fence for a minute, but then he closes the door and steps closer, accepting Dean’s offering and taking an extremely generous gulp. Dean cocks his head at him. “Rough day?”

The guy exhales heavily through his nose and slumps onto the other bench seat, at a ninety-degree angle from Dean’s. “Any day I’m forced to spend in close quarters with my infuriating brother is a ‘rough day.’” He turns a full-on glare on Dean, and holy fuck, those eyes are even more amazing up close. “Every day has been a rough day lately.”

“He in the band too?”

The guy nods resignedly. Dean reaches for the flask back and takes another sip. “You guys always take on jobs together?”

Blue Eyes does a half-shake-half-shrug. “It’s a relatively recent development. We lived out in the country all our life, but… well, I don’t want to bore you with the whole story, but we were forced to move out of the family home. We’re both decent musicians, and Gabe had some experience playing clubs in Chicago, so he convinced me to come with him and settle in the city.”

“So you haven’t been in Chicago long?” Dean asks, trying hard to sound casual.

The guy shakes his head. “Just a few months.”

Dean cheers inwardly. Maybe Blue Eyes just hasn’t gotten around to exploring the scene yet. It’s still a long shot, and Dean’s still got a rich heiress to find. But a warm body to enjoy for a few days, especially when it comes with a face like that? Dean’s not one to turn that down. “I’m Dean.” He sticks out his hand and the guy leans forward to shake it.

“Castiel. Cas, for short.”

“Nice to meet you, Cas.” Dean dials up the wattage on his smile, just a little. He might be kidding himself, but he thinks Cas looks a little bashful when he smiles back. _Maybe the guy is just awkward_ , Dean reminds himself. _Keep your pants on, Winchester._

Something occurs to him. “Hey, uh, Cas? You’re not gonna tell on me, are you?” At Cas’ interrogative eyebrow, he adds, “About the bourbon, I mean. It’s just, Adler’s got his eye on me already. I wouldn’t put it past him to kick me outta the band over a little thing like that.”

“Of course not, Dean,” Cas says, still serious as all hell. “I’m just as guilty as you, after all.” An actual goddamn tease of a sparkle gleams in his eyes. “You wouldn’t tell on _me_ , would you?”

That’s a flirtation. Dean’s almost certain of it.

“Wouldn’t dream of it,” he says, and his smile could probably power an entire goddamn apartment building by now. “So what d’you play, Cas?”

“Bass fiddle. What about you?” Cas leans forward, forearms resting on his thighs, like he’s about to pay really close attention to what Dean has to say. It’s a little unnerving.

Dean shrugs and drapes himself over the seat again, one leg up, putting the inside of his thigh on display just a little. “I sing, and I play the ukulele.”

Cas snorts.

“Hey,” Dean says, slapping at Cas’ arm half-heartedly across the space between their benches. “It’s a very dignified instrument.”

Cas’ lips twitch in the smallest possible approximation of a smile. “Of course, Dean.”

Dean chuckles. “Nah, you’re right. I mostly play it for its entertainment value. People think it’s hilarious, a big guy like me playing a tiny instrument on stage.”

“Did you come from a musical family?”

“Sure,” Dean says, grinning again, a lopsided, suggestive one this time. It’s the one that’s been known to weaken the knees of women, and a few men, across Illinois and surrounding states. “My father was a conductor.”

Cas sits up a little, clearly impressed. “Was he really?”

“Uh-huh,” Dean says. “On the Baltimore and Ohio.”

Cas squints at Dean, looking deeply confused. “The train?”

“Yeah — conductor, train conductor? It’s a joke, Cas,” Dean prompts. “Not a great one, sure, but you’ve heard of those, right? Jokes?”

Cas holds out his hand in silent demand, and Dean passes him the flask. Cas takes a thoughtful gulp. “You know what’s a joke? Before we left for this trip, my brother spent the last two dollars we had on a dog called Greased Lightning, and it came in last.” He takes another sip, then adds, completely deadpan, “Maybe if they hadn’t greased it, it would have run faster.”

Dean laughs so hard, he falls off the damn seat. So much for his subtle methods of seduction.

***

“What is this, ladies and gents? A funeral?”

At the tapping of Donna’s conducting stick against the top of the nearest seat, the sound of instruments subsides with a vague plucking of strings and a literal sad trombone sound from Charlie.

All sixteen band members have gathered at one end of the compartment, standing or sitting or leaning onto seats, as their instruments allow. Cas slumps wearily against the neck of his bass fiddle. 

This is the third time Donna has cut them off on this particular song. It’s almost as though practicing in a cramped space, aboard a moving train, isn’t an ideal situation. He supposes this is the sort of thing he’ll have to put up with, going on the road with a band.

“Let’s try this again, and goose it up a little this time,” Donna says, straightening up with a determined nod that makes her black-and-white fascinator sway dangerously on top of her head. She shakes out the sleeves of her embroidered coat and raises her conducting stick. “One, and a-two, and a-three.”

On three, the tune starts up again, everybody noticeably working to pick up the tempo. Cas’ fingers fly over the strings of his bass, plucking at them with slowly increasing enthusiasm, swept up in the swinging rhythm as the song continues without interruption. Slowly, he feels a grin spread across his face, the kind of lightness he only gets when he’s playing. In a fit of exuberance, he spins the bass on its stand, catches it and starts plucking again, slowly picking up even more speed to match the rhythmic rise and fall of Donna’s hands. Next to him, Gabe is clearly getting into the spirit of things too, running up and down the scales on his sax with a pleased twinkle in his eye.

Almost involuntarily, Cas’ eyes find Dean, the handsome new friend he made in the smoking room earlier. Dean is perched on an armrest, holding his ukulele and strumming away at it, somehow managing to look charming rather than ridiculous as he hunches his broad shoulders over the tiny instrument.

Dean catches Cas’ gaze on him and grins. Cas knows Dean’s solo is coming up, and sure enough, at the cue from Donna, Dean gets up, squaring his shoulders and grinning widely as he sings the first two lines.

_Runnin' wild, lost control_

_Runnin' wild, mighty bold_

Dean lowers his ukulele and starts to strut down the aisle between seats, pivoting on his heel and walking backward to face the band as he rumbles through the lyrics in a cheerful, honeyed baritone.

_Feelin' fine, reckless too_

_Carefree mind all the time, never blue_

Dean reaches the end of the compartment, where Adler is sitting with his back turned to the band, filling out some kind of paperwork. With a pointed glare down at Adler’s bald pate, Dean struts forward again, shimmying his hips a little. Cas is so mesmerized, he almost forgets about keeping the bass line going.

_Always goin', don't know where_

_Always showin' I don't care_

Dean spreads his arms to belt out the last two lines, stretching the vowels like rubber bands.

_Don't love nobody, it's not worthwhile_

His eyes meet Cas’ again, and he winks, so quickly that Cas is almost sure he’s imagined it. Dean’s eyes sparkle as he practically shouts the last word of his solo.

_All alone, runnin' wild!_

With a final shimmy and a spread of his arms, he walks back to rejoin the band, which is still playing, transitioning into the next piece. As he squeezes past Donna, the edge of his suit jacket snags on one of the seats, and something metallic hits the floor with a loud _clunk_.

_The flask_ , Cas realizes with a start.

The music stops from one split-second to the next. In the silence, all the way at the other end of the compartment, Adler’s head shoots up from his pile of paperwork. Donna freezes, looking down at the flask as Adler stalks over.

“What’s this?” he demands, picking up the offending object.

Veins thrumming with a sudden surge of adrenaline, Cas holds out his hand. “It’s mine, Mr. Adler. I do apologize. I wasn’t aware of the policy regarding alcoholic beverages, and I’ll certainly make sure not to indulge going forward.”

Adler’s eyebrows meet across his over-large nose. “I should hope so, Mr. Novak.” He hands the flask to Cas, somewhat reluctantly. “I’ll return your property, but I’ll be watching you very closely. I have no qualms about dismissing you at the next station, I assure you.”

Trying to look suitably chastened, Cas accepts the flask and stores it in his jacket pocket. As soon as Adler turns his back and stalks off, Cas looks over at Dean, who has returned to his seat on the armrest. His face is slack with a mix of awe and appreciation. “ _Thank you,_ ” he mouths, and flashes a small, shy smile that’s nothing like the cocky grins Cas has seen so far.

Cas is extremely grateful he plays an instrument that’s sturdy enough to support his weight. He’s not sure his legs could manage on their own at the moment.

*** 

Cas pictures Dean’s smile later that night, as he lies in the top bed of Bunk 7 in the men’s dormitory section of the train carriage, separated from the women’s section by nothing but a heavy velvet curtain.

It’s a rather nice change of pace from the thoughts that occupied him while they were still within the city limits, considering that they mostly revolved around his gruesome murder at the hands of Spats and his associates.

Even as his blood simmers at the memory of how Dean’s plump lips shaped themselves around that whispered “thank you,” Cas reminds himself sternly that it would be inappropriate to engage in any… activities at the moment. There are nearly twenty other people within earshot, some of them female. Not to mention, one of them is the object of his unsanctioned fantasies. Cas glares down at his lap, willing the stirring there to subside.

At that exact moment, the curtain drawn all the way around his bunk opens on the left-hand side, and a head pokes in through the gap.

“Hey, Cas.” Even in the semi-darkness of the train’s subdued night lighting, Dean’s teeth gleam white as he smiles. Seeing that smile in real life is a rather unnerving development, given the recent trend of Cas’ thoughts. 

“Dean?” Cas shoves upright and promptly hits his head on the ceiling of the compartment.

Dean hauls himself up the ladder and into Cas’ bunk, stretching out next to him on the already-cramped mattress.

“Hey, I just wanted to come over to say thanks for covering for me,” Dean says, fidgeting to arrange himself into a semi-comfortable position. He ends up on his side, facing Cas, one cheek propped on his hand. “You’re a real pal.”

“It’s nothing,” Cas says, extremely conscious of where his shoulder is brushing against Dean’s arm. He wiggles toward the right side of the bunk to minimize contact with Dean’s warm, tempting skin. Dean still smells a little like bourbon, mixed with pomade and aftershave, and a delicious top note of comfortable, sleep-rumpled scent.

“It _ain’t_ nothing, Cas,” Dean says, earnestly. “If it hadn’t been for you, Adler would’ve kicked me off the train. I’d be out in the middle of nowhere right now, sitting on my ukulele.”

Cas snorts, and immediately stifles the sound with his hand. In addition to his policy on alcohol, Adler was also very clear about his views regarding after-hours bunk visits. Still, Cas says, voice shaky with mirth, “I don’t think your ukulele would survive being sat on.”

Dean chuckles. “Good point.” There’s a beat of silence, then, “D’you still have the flask? It’s kind of… a family heirloom.” Something about Dean’s eyes tightens when he adds, “Was my dad’s.”

Cas nods and almost leans across Dean to get to his suit jacket, which is hanging on a hook next to his bed. But he thinks better of it. “It’s, uh. If you open the curtain right there behind you, it’s in my jacket. Inside pocket.”

Dean nods his thanks and retrieves the flask, lying back on Cas’ mattress and turning the small metal object over and over in his hands. As the quiet of the dark bunk settles around them, Cas becomes extremely conscious of the soft sound of Dean’s breathing, and how they’re close enough that it’s almost impossible not to touch. It would be so easy, and Cas could have sworn Dean was being flirtatious during their conversation in the smoking room earlier. 

Still, it doesn’t do to be hasty about these things.

Cas has just begun debating the wisdom of edging a little closer to Dean, maybe resting the back of his hand against the side of Dean’s leg — both gestures subtle enough that they could be interpreted as pure accident — when Dean says, “Hey, Cas? You don’t have any more booze, do you?”

Cas shakes his head regretfully. “No.” His mind casts around for other excuses to keep Dean in his bed just a little while longer, when a brilliant idea occurs to him. “But I know where we can find some.” Feeling daring, he adds, “Don’t move,” and grins at the small salute Dean gives him in response.

The bunk beds have ladders on both sides — a small mercy, because it means Cas can climb down without having to scoot across Dean’s rather tempting lap first. He makes his way down and creeps to the far end of the bottom bunk, where Gabe is sleeping. He pulls open the curtain just a tad, right at the bottom of the bed, where he knows Gabe keeps his suitcase.

Cas sticks his head through the gap and looks over at Gabe, who’s curled up peacefully on his side, snoring a little. Carefully, Cas eases the suitcase open. The neck of a bottle of whiskey pokes out from a messy pile of shirts and socks.

Cas pulls it out and makes his retreat. He grabs hold of the handrail on the ladder and looks up, locking eyes with Dean, who’s peeking out from between the curtains of Cas’ bunk.

Knocked off balance by the green of Dean’s eyes even in the low light, he just barely manages to hang on to the ladder, but loses his grip on the bottle.

It falls to the floor with a heavy _thunk_.

Cas freezes, Dean’s eyes widening above him. When no one immediately stirs, Cas hurries back down the ladder and retrieves the whiskey.

“How’s the bottle?” Dean whispers.

Cas holds it up with a triumphant grin. “Half full.”

He traipses back to the ladder just as the curtain around Gabe’s bunk moves. Gabe’s head pokes out, one hand pulling sleepily at his face. “Baby bro?” His eyes fall on the bottle in Cas’ hand, then move to the undoubtedly guilty look on his face. “What’re you doing with my stash there, Cassie?”

Cas tries his best to look affronted and dignified. “Just borrowing it,” he hisses. “Don’t worry, we’ll leave you plenty.”

Gabe’s eyebrows rise to meet his hairline. “‘We?’”

Inwardly cursing himself, Cas attempts to construct a plausible explanation for his slip; one that will discourage Gabe from investigating further. But, once again, his brain deserts him in his hour of need.

Gabe scrambles off his mattress and looks up. From above, Dean gives a small wave. “Well,” Gabe says, grinning like the Cheshire Cat. “Isn’t _this_ interesting? Am I interrupting a tête-à-tête?”

Cas doesn’t know what to say to that, but he knows he’s blushing furiously and he’d like to preserve at least some of his dignity tonight. He really wishes he could find it in himself to look at Dean and gauge his reaction.

“Just go back to bed, Gabe,” he growls.

Impossibly, Gabe’s grin widens. “I think I’ll stop by yours instead,” he says, and scrambles up the ladder. Cas follows right on his brother’s heels, hoping to minimize his chances of further embarrassment in front of Dean. He’s barely reached his bunk and folded himself awkwardly near the bottom of the bed when the curtains open yet again and a woman with bobbed red hair looks in. “Evening, gents!” she whisper-shouts. “Having a party? Can I join?”

Cas is about to object when he catches sight of the bright grin on Dean’s face. 

“Anytime, Charles.” Dean gestures at the newcomer. “Not sure if you guys have met officially, but this is Charlie Bradbury.” He inclines his head at Cas and Gabe in turn. “This is Cas, and…”

“Gabe. Cassie’s brother,” Gabe supplies, and reaches out a grabby hand for the bottle. With a weary sigh, Cas passes it to him.

Charlie starts telling a long-winded joke about a one-legged jockey, and Cas shifts his leg to get more comfortable. It bumps into Dean’s foot. Startled, Cas looks up and finds Dean’s eyes already on him, warm and maybe a tad apologetic.

Cas shrugs and rolls his eyes dramatically in the direction of his brother, who is shaking with not-so-silent mirth at the punch line of Charlie’s joke. (“Don’t worry about me! I ride side saddle!”) 

Dean chuckles. They trade a small smile, and Dean shifts his foot so it’s tucked just slightly under Cas’ leg.

Maybe this night won’t be a total loss after all.

**Notes for the Chapter:**

> Drag balls in Chicago's South Side were [a real thing](http://www.encyclopedia.chicagohistory.org/pages/509.html)!


	2. Chapter 2

**Notes for the Chapter:**

> The most fashionable resort in 1920s Palm Beach was called The Breakers, but the descriptions of the hotel in this fic are based on the [Hotel del Coronado](https://hoteldel.com/timeline/like-hot) in San Diego, where Some Like It Hot was filmed. 
> 
> There are two songs in this chapter. One is "I Wanna Be Loved By You," famously performed by Marilyn Monroe in the movie. The other is "Masculine Women, Feminine Men," a real hit song from the 1920s. You can listen to some recordings of it and learn more about its significance from a queer perspective [here.](https://www.queermusicheritage.com/MWFM.html)

The shuttle bus for the Palm Beach Coronado Hotel rattles along the waterfront promenade, and Cas curses every roar of its engine, every bump of the wheels on uneven pavement. But above all, and with great conviction, he curses the too-bright Florida sunshine streaming in through the open windows.

Perhaps he shouldn’t have accepted those swigs from Charlie’s bottle of gin on top of the whiskey last night.

His memories are hazy, but he does remember falling asleep on something warm and rather comfortable. When he woke up, he was alone, nothing for company but a rumpled top sheet and a pillow with a distinctly alcoholic odor to it.

As he shrinks away from the window, trying and failing to shield his throbbing head from the relentless rays, he wonders miserably whether he might have made any unwanted advances on Dean.

Of course, he could ask the man himself, but Dean is currently sitting five rows away, near the front of the bus, laughing much too loudly at a comment of Charlie’s. 

Never mind the fact that the prospect of asking Dean that kind of question is more than a little mortifying.

Asking Gabe will undoubtedly result in relentless teasing, but at least he’s already aware of Cas’ preference for the male form. And he’s conveniently sitting less than a foot away.

Steeling himself, Cas leans over to mutter, “Gabe?”

Gabe hums absently to show he’s listening, but his eyes remain closed, and he resembles nothing so much as a happy cat sunning itself. His decision to claim the aisle seat was clearly nothing but pure, unadulterated cruelty. 

“Did I… embarrass myself last night?” Cas asks.

Gabe opens his eyes and cackles. “You usually do, baby bro. You’ll have to be more specific.”

Cas takes a deep breath, hoping he’ll somehow manage to inhale the patience he needs to endure his brother. It doesn’t work. “You know damn well what I mean,” he hisses. “Did I… try anything? With…” He grimaces and jerks his chin forward, to where Dean’s booming laugh is again audible halfway down the bus.

“Noooo…” Gabe says, stretching the word out along with his arms, “…ooot unless you count falling asleep with your head pillowed on his leg, like a faithful little lapdog.”

Cas gapes. Outside the window, palm trees line a pristine beach, the ocean glittering azure. For all Cas cares, the bus might be driving them past the Seventh Circle of Hell. “I didn’t.” He grabs hold of the sleeve of Gabe’s jacket. “ _ Please _ tell me I didn’t.”

“Wish I could, Cassie,” Gabe says, clearly enjoying Cas’ mortification. “If it helps, Dean-o fell asleep too. Drooled on your pillow and everything.”

Cas rubs at his nose with his forefingers, squeezing his eyes shut. “I’m sure you and Charlie had a good laugh at our expense.”

“Actually,” Gabe says thoughtfully, “Charlie told me a very interesting thing. Apparently, young Dean over there is just as inclined to enjoy the company of men as women.”

Cas’ heart attempts to perform a skip-hop at this information, but he’s too hung over and embarrassed to let it. “So what if he’s attracted to men,” he growls. “That doesn’t mean he’s attracted to  _ me _ . Especially as I apparently decided to impersonate a Scottish terrier last night.”

“More like a wiener dog,” Gabe retorts, eyes twinkling with amusement at his own joke. He dodges the slap Cas aims at him with the ease of twenty-five years’ practice.

Cas chooses to save his dignity by lapsing into complete silence for the rest of the ride. Not five minutes later, the bus hops the curb and roars up the curved driveway to the hotel that will be The Dapper Donna Orchestra’s home for the next three weeks. 

The Coronado has the look of an overly fanciful fairy-tale castle, with its tall turrets, endless chaos of gabled roofs, and annexes sitting on top of and alongside each other. The view coming up the driveway is dominated by a large, octagonal pavilion tower, flanking a generously sized porch. As the bus pulls up in front of the main entrance, Cas spots a line of wooden rocking chairs along the porch, all occupied by elderly gentlemen in white suits and Panama hats, peeking over the tops of their  _ Wall Street Journals _ at the newcomers while pretending not to do so.

Cas stumbles off his seat after Gabe, cursing his too-warm woolen suit and pulling at his stiff shirt collar. He thought pawning his linen two-piece was a good decision, back when the resulting eight dollars bought him several days’ worth of meals. Now, it seems distinctly unwise.

He follows the other band members into the cool, blissfully darkened interior of the hotel lobby, whose opulence he suspects would put Buckingham Palace to shame. Cas’ eyes fall first on the massive chandelier that dominates the center of the room, and he wonders idly how many people would be killed if it came unscrewed. He decides the number is somewhere in the neighborhood of a dozen and takes a deliberate step back, out of range.

Persian carpeting lines the entirety of the floor, and mahogany columns rise up to meet the equally dark beams of the ceiling. On the second floor, a promenade in the same shade of dark wood surrounds the lobby on three sides.

Next to a flower arrangement, squarely in the middle of certain chandelier death, stands Adler, clutching his beloved clipboard. He clears his throat fussily to attract the attention of the band members, who are milling about various parts of the lobby — or just staring at it, slack-jawed.

One by one, everyone shuffles over to form a half-circle around Adler, who’s now flanked by Donna. Adler takes a deep breath, but Donna’s cheerful alto interrupts him before he can fully puff up for whatever tedious speech he was about to deliver.

“Not bad, eh?” Donna says genially. “Mr. Adler’s got your keys and room assignments. We’re on for our debut performance at eight, downstairs in the clubroom. Just everyone have a good time till then, and don’t be late, will ya?” She grabs a key from the small pile on the side table at Adler’s back, then gives the group a cheerful wink as she turns to go. “No roommate for  _ me _ . Perks of bein’ the boss.”

Adler levels Donna’s retreating back with a deeply disapproving glare before he turns back to face the musicians. “Very well, if you’ll just step forward one by one as I call your name…”

Immediately, Adler is swarmed by more than a dozen men and women, all of whom are trying to peek over his shoulder at the clipboard or retrieving keys at random. From the maelstrom, Adler can occasionally be heard to exclaim things like, “Remember, Bradbury, curfew is at midnight,” or “Fitzgerald, I must insist that you keep your elbows to yourself.”

Cas looks on in quiet bewilderment. He’s long since lost sight of Gabe, who was one of the first to join the fray. But the first one to emerge from it is Dean, looking slightly rumpled and somehow even more attractive for it. He walks straight over to Cas, a broad grin on his face, dangling two keys emblazoned with the number nine on a small orange pendant. “Hey, Cas. Looks like we’re roommates.”

Somehow, Cas’ blood manages to rush simultaneously to and away from his face. “We… are?”

“Yeah.” Dean shrugs. “I usually room with Garth, and I figured you were gonna room with your brother.” His grin takes on a teasing edge, and he bumps his shoulder against Cas’. “Did you ask to room with me, Cas?”

Cas’ blood has  _ definitely  _ decided to stay put on his face now. “No, I… I wouldn’t… not that I mind…”

Dean chuckles. “Don’t fret, Cas. It’s fine. We’re gonna have a great time together.”

Hoisting his suitcase and instrument case in one hand, Dean tosses a key to Cas with the other. Cas catches it and trails after Dean to the elevators, too preoccupied to notice the way Dean’s grin slides off his face, replaced by a worried frown. 

*** 

For as long as Dean can remember, love has gotten him into trouble. Going hungry as a kid to feed his lanky, skinny little brother, who still left Dean and their ma behind as soon as he got old enough. Getting his heart broken by his first girlfriend, when it became clear that he wasn’t going to be developing any “prospects” any time soon. Getting punched in the face the first time he ever tried something with a guy he liked.

So, no, Dean’s not looking to fall for anyone, now or ever. For years, he’s taken his fun where he could get it and never asked for anything else.

Which is why the previous night has been on his mind.

He doesn’t remember falling asleep in Cas’ bed, but he does remember waking up. It was just the two of them — Cas curled up with his head resting above Dean’s knee, squarely on the meat of his thigh.

He dislodged Cas as best he could, which involved a lot of awkward maneuvering, but thankfully, Cas never woke. Before Dean hopped onto the ladder to climb down from the bunk, he took a last look at Cas’ sleep-soft face, the slight wrinkle of his forehead, the slack bow of his lips. By the time Dean realized he was staring, he’d already started counting the coal-black lashes resting on Cas’ cheeks.

Tamping down on the warmth in his chest, Dean headed back to his own bunk, reminding himself that all he was ever going to have with Cas was just a bit of fun. A flirtation, maybe a kiss. If he was really lucky, a hasty, drunken encounter after one of their performances.

Because Dean’s got a rich heiress to find and marry, and that’s that.

Of course, the universe itself seems to be conspiring against him, because, by some cruel twist of fate, he’s going to be rooming with Cas. Night after night, undressing next to each other, and morning after morning, watching those blue eyes squint at him from under a head of sleep-rumpled hair. It’s not the ideal scenario for a meaningless, no-strings-attached dalliance.

Maybe, Dean thinks, glaring at their pair of twin beds while Cas deposits his overnight things in the bathroom, he can arrange for housekeeping to supply a divider curtain. Remove the temptation to act on his attraction. Out of sight, out of mind.

A cheerful knock startles Dean out of his thoughts. “I’ll get it,” he calls in the direction of the bathroom. He opens the door to reveal Garth on the other side, grinning broadly.

“Hiya. A few of us are heading to the beach. You and Cas feel like joining?”

Dean’s mood lifts immediately. Just what he needs: time in the sun, away from this too-small room and its devastatingly handsome occupant. “I’ll come,” he says. “Not sure about Cas. He might be busy.”

Not to be deterred, Garth calls, “How ‘bout it, Cas? Are you busy?”

Dean turns to find Cas stepping out of the bathroom, looking a little sheepish. “I, uh… yes. I was… planning to take a bath.”

“A bath?” Garth asks, incredulous. “With a perfectly good ocean just outside?”

Cas shrugs. “I don’t…” His shoulders slump, forehead creasing in a frown, and Dean has to resist the sudden urge to kiss that frown away. “I don’t have a bathing suit,” Cas admits finally, looking like he expects to be dismissed from the band immediately in the wake of his admission.

“Pshaw,” Garth says, dispelling Cas’ concern with a wave of his hand. “I’ve got an extra one you can borrow.”

Cas’ eyes rove up and down Garth’s frame: tall, sure, but a whole lot skinnier than average. “I’m not sure we’re… the same size?”

“Eh, close enough. C’mon.” Garth strides from the room, motioning for Cas to follow, and, with a helpless look at Dean, Cas does.

He returns a few minutes later, clutching a navy-blue bathing costume. “Garth says he’ll meet us down there,” Cas says, looking somewhat chagrined.

Dean swallows, nods and grabs his own swimsuit. They set off downstairs in silence, following signs for the beach until they reach an exit near the back of the lobby. There’s a line of changing huts close to where the paved path gives way to immaculate white sand, and they each duck into one. Dean forces a smile and a jaunty, “Well, see ya on the other side!” then winces immediately at his own awkwardness. 

He’s the first one to emerge; there’s no sign of Cas except for a string of barely muffled curses coming from the hut where Cas disappeared earlier.

“Everything alright in there?” Dean calls.

“Fine,” Cas grumbles, just loud enough to be heard through the closed door. “As I suspected, this suit doesn’t fit me very well, and it’s a pain to get into.”

Dean prays for strength, clutching his pile of clothes and the beach towel he grabbed off a stack in the changing hut. It takes only another minute for Cas to emerge, and as soon as he does, Dean knows his prayers have fallen on deaf ears.

Like Dean’s bathing suit, the one Cas is wearing is a two-piece, consisting of a sleeveless shirt and belted shorts made from a sleek, clinging jersey fabric. Up until a few years ago, men’s swimsuits came with modesty skirts to conceal everything below the midsection and above the knee, but that fashion has recently fallen out of favor.

All of which means that Dean has an excellent view of a pair of well-formed, muscular thighs that are barely contained by Cas’ shorts. And if Dean lets his eyes wander just a little bit further north, he can see the outline of… he averts his eyes. His ma may not be the best cook, but she didn’t raise a son who stares at other people’s private parts. At least, not in public.

Still, the glimpse he did catch seems to have entirely disabled Dean’s already mediocre ability to think before he speaks. It’s the only possible explanation for why he says, “You, uh. You ride horses or something, back in the country?”

Cas frowns, confused, before he notices the direction of Dean’s stare, which has dropped helplessly southward again, to those sturdy, delectable thighs. “Yes,” he says, tilting his head like someone trying to recall an elusive memory. “I used to ride. Every day, in fact. I enjoyed it very much.” He sounds a little wistful.

“Interesting hobby for a penniless musician,” Dean says idly, turning away to walk the rest of the way to the beach, in hopes that he’ll find a much-needed distraction there.

Cas doesn’t respond, or follow, and Dean looks back to find Cas’ lips slightly parted, eyes fixed unmistakably in the region of Dean’s backside.

“Uh, Cas?” he asks, a slightly amused lilt to his voice. “You with me there, pal?”

Cas blinks slowly, and immediately flushes. “My apologies, Dean. I was… lost in thought.”

Well. This, Dean can work with. Easy, flirtatious banter is where he’s at home. He lets his smirk drift further into lascivious territory as he asks, “Lost in thoughts of my shapely rear?” 

Impossibly, Cas’ flush deepens further, until he’s almost purple. “I… don’t know what you mean.”

Dean shrugs, loose and easy, and starts walking, Cas trailing along behind him. And maybe he puts on a bit of a show, adds just a little extra shimmy to his walk. He can still have fun, can’t he? Get that kiss he was hoping for, as long as he doesn’t lose sight of the fact that that’s all it is: fun. 

If there’s anything Dean knows, it’s how to indulge himself without letting his heart call the shots.

“It’s alright, Cas,” he says, when Cas catches up to him. “You can look. I don’t mind.”

Dean watches Cas’ Adam’s apple bob with a heavy swallow. “I don’t… want to make you uncomfortable,” Cas says quietly. “Or, you know. Draw attention.”

Dean bumps his shoulder into Cas’; gently, just enough to jostle him a bit. “You don’t have to watch yourself around  _ me _ , Cas. Or the other members of the band either.” He purses his lips, considering. “Well, except for Adler. He’s a judgmental prude.”

Cas looks up and down the path to the beach. There’s a few other people walking along, but no one within earshot. Still, Cas lowers his voice just a bit more when he says, “I suppose you’ve guessed by now, but I do prefer…” He exhales a deep breath. “The company of men. If you think it’s inappropriate to room together under the circumstances, I understand. I’m still not entirely sure how we were assigned to the same room in the first place.”

A smarter man than Dean _ would  _ agree to switch rooms, just to make sure everyone’s hands stay strictly above the belt and no one gets distracted from foolproof schemes to lure rich heiresses into the marriage bed. But Dean is Dean, so he says, “It ain’t a problem, pal. Probably won’t see much of me anyway. I’ve got big plans.” He winks, and Cas’ face, only just recovered from its most recent blush, pinks once more. 

“What plans?” Cas croaks.

They’ve reached the beach now, bare toes sinking into soft, white sand. A gentle breeze ruffles the surface of the gleaming, bright-blue ocean ever so slightly, the soft  _ whoosh _ of waves offset by the cantankerous cawing of seagulls. The perfect day.

“Plans to get set up for life,” Dean says cheerfully, spreading out his towel and lowering himself onto his front.

Cas snorts as he spreads out his own towel next to Dean’s. “Are you planning to rob a bank?”

“The next best thing,” Dean says, closing his eyes and resting his cheek on his folded arms, soaking in the sunshine. Undoubtedly, he’ll freckle something awful in short order, but the warmth feels too nice for him to care, after months of Chicago winter. “I’m going to find an heiress to marry.”

Cas is silent for so long that Dean opens his eyes, just to check if the guy’s managed to fall asleep already. He hasn’t. In fact, he’s lying on his stomach as well, and he’s got those unfairly attractive blues trained on Dean, studying him. “You’re going to marry for money.”

“Sure,” Dean says, shrugging. He turns onto his back, closing his eyes against the sunlight. “I mean, this place, right here?” He gestures expansively behind them, at the massive complex of the hotel. “It’s lousy with rich girls, I’d bet you anything. They’re just waiting to be knocked off their gams by my roguish charm.”

Cas flips over too, once again putting the tight fit of his bathing suit on display. Dean fights down the urge to sneak a peek. 

“You’re serious,” Cas says, flatly.

“As a heart attack. That’s what I’m here for. Meet a rich girl, become a kept man and offer my ma back home the kind of life she deserves and never got to have.” It’s God’s honest truth, but for some reason Dean can’t fathom, the words feel heavy on his tongue.

Cas looks back at him, expression unreadable. “I suppose being rich does have its advantages,” he says, slowly, as though he’s picking his words. “But it’s not something I expect will ever happen to me again.”

Even sun-sluggish as Dean’s brain is, it snags on that small word —  _ again _ . But he has no time to investigate further, because Charlie is jogging up to them across the sand, green swim cap glinting wetly in the sunlight. “C’mon, fellas! You can sleep later. We’re having a game of volleyball.”

Dean squints at her, shading his eyes with his hand. “You’ve never once in your life been this excited about physical activity. Admit it, Charles. All you want is a chance to watch Dorothy jump up and down in that cute little swimsuit of hers.”

Charlie grins wickedly, eyes sliding to Cas and his criminally undersized pants. “Look who’s talking.”

Dean growls at her and scrambles up. “Just for that, I’m playing to win.” He turns around to face Cas, who’s squinting after the two of them somewhat forlornly. “You coming, Cas?”

Cas groans. “I don’t know if movement is compatible with my idea of fun at the moment.”

The sun and the prospect of a competition have Dean feeling giddy and reckless, so he bends down to grab Cas’ hand and pull him up. “C’mon, sunshine. Let’s show these girls how it’s done.”

Cas rolls his eyes, but says “fine” and follows Dean and Charlie to where a net is set up in the sand, a volleyball court marked off around it with white tape. The girls — Charlie, Dorothy, Lydia and Gilda — are already lined up on the far side of the net, their swimsuits and caps a riot of red, blue, green and yellow. On the other side, Garth and Lee are waving for Dean and Cas to join them.

Charlie opens the game with an aggressive serve that immediately lands in the far back of the boys’ territory, barely missing Garth’s flailing arms.

To Dean’s surprise (and not insignificant arousal), Cas launches the ball back across the net with a well-aimed, powerful smack that nets the men’s team an immediate point when Dorothy dives for the ball and misses. First horseback riding, and now this? Dean scowls, wondering what cruel and capricious God he’s offended, to be presented with the perfect man at exactly the wrong time. The thought is so distracting that he misses the next ball, which should’ve been an easy catch by anyone’s definition.

For the next ten or fifteen minutes, they try to keep track of the score, but the game soon descends into squealing, shouting and the occasional bout of playful wrestling.

When it’s Dorothy’s turn to serve, Charlie aims a strategic poke at her midsection and the ball goes far off course, bouncing away into the sand. Buoyed by the low, rumbling sound of Cas’ laughter next to him, Dean calls, “I’ll get it” and bounds after the thing.

He’s so busy trying to look good as he jogs away that he misses the straps of a purse, coiled in the sand like a rabbit snare. His foot catches on the leather and he goes down, landing painfully on his front. 

The first thing he sees when he pushes himself up is a pair of crossed legs, extremely shapely, tapering into painted toenails. The owner of said legs is sitting in a roofed basket chair, and therefore mostly in the shade, but Dean can make out a slim silhouette encased in an emerald green bathing suit. The top half of the woman's face is hidden behind an oversized pair of sunglasses, but the bottom half shows off a pair of sinful lips. She’s definitely a looker, her face framed by a flowing mane of wavy hair that’s colored a deep, carmine red Dean knows doesn’t exist in nature. 

He grins. “Apologies, ma’am. Very clumsy of me.”

The vision removes her sunglasses, one corner of her lips curving up wryly. “I suppose it was my own fault for leaving my purse in the sand. Although, if I’d known handsome men would be throwing themselves at my feet, I’d have tried it much sooner.”

Her eyes, glinting darkly in the shadow of the roof, rake over Dean’s chest in frank appreciation.

“You’re not hurt, are you?” she asks, in the slightly bored tone of someone who understands the well-being of other people is something one ought to be theoretically concerned about.

Dean opens his mouth to answer when Cas jogs up behind him. “Dean, are you alright?”

“’m fine, Cas,” Dean mumbles, feeling a little foolish because he’s still on his knees, looking up at Cas on one side, his new acquaintance on the other. “Just tripped, that’s all.”

He gets up and dusts himself off. Cas looks him up and down, but seems satisfied that Dean isn’t in any danger of keeling over again. “Are you coming back? We’re still playing.”

Dean almost says “sure,” but then he catches the eye of the redheaded mystery woman again, her gaze still openly appreciative.

“Actually, if you can spare your friend here for a moment, I wouldn’t mind continuing our conversation,” she says smoothly, addressing Cas, but her eyes never leave Dean’s.

Dean takes in the gleam of crystal on the woman’s pendant earrings — her well-manicured left ring finger, very much unencumbered by a wedding band. This is exactly what he came here for, isn’t it?

He’ll deny to his dying day that his heart sinks a little before he turns to Cas and says, “You go ahead. I’ll join you back at the room later.”

Cas looks disappointed, but nods and grabs the wayward ball, trotting back to join the others.

“What might your name be, handsome stranger?” the woman drawls, even as Dean looks around for a place to sit down. There isn’t enough room in the basket chair for two people, and the next one over is too far away to keep up a conversation, so he lowers himself back onto the hot sand. 

“Dean Winchester,” he says, holding out his hand to shake.

The woman reaches down to take it, chuckling throatily. “A pleasure. Josephine Knight. But you…” She holds on to Dean’s hand just a little longer than politeness calls for. “You may call me Josie.” She leans back in her chair, making a big show of fluffing out her hair before she adds, “You’re sure you’re not hurt?”

“Positive,” Dean agrees, shifting his rear to get more comfortable. “It’s great to make your acquaintance, Josie.”

Josie nods, satisfied. “It seemed a good idea to check. You see, I’m one of the Texas Knights. My family owns the Knight Oil and Flammables empire. As you might imagine, we have considerable means, and it wouldn’t be the first time someone hired a shyster lawyer to sue us for an imaginary injury.”

Dean swallows down his irritation at the comment, forcing his smile to remain in place. Knight Oil is a household name, and even in Chicago, it’s well known that the Knights have enough money to buy the entire state of Texas. Lucky on his first try. “Now I _ am _ hurt,” he says easily. “To think such a lovely woman has such a low opinion of me.”

Josie smirks. “Improve it, then. What do you do when you’re not busy looking dashing, Dean Winchester?”

“I sing, and I play the ukulele,” Dean says, forcing himself to look pleased rather than self-conscious at the admission. He’s not ashamed of his career, particularly, but he doubts it’ll do much to impress an heiress. Well, he thinks to himself, flexing his broad shoulders, he has other assets he can use to win her over. “I play with The Dapper Donna Orchestra, up at the hotel.”

“Ah,” Josie says, expression unreadable as she pulls her purse into her lap and retrieves a gilded cigarette box. She removes a cigarette, taps it against the lid, and Dean curses himself for leaving his suit pants with his towel. They always contain a lighter. As it is, Josie lights up with a match of her own, and says, on the exhale of the first puff of smoke, “Jazz band, isn’t it?”

“Yeah,” Dean agrees, warming to his pet subject immediately. “We’re pretty damn good, actually. Fast, catchy and hot.”

Josie’s lips curve lasciviously around another drag of her cigarette. “Well, some like it hot, I suppose,” she says, eyes lingering on the line of Dean’s exposed shoulder.

Anticipation buzzes under Dean’s skin at the suggestive edge of that look. He knows a sure thing when he sees it. Hitching on his most charming smile, he says, “Well, if you find that you’re in the mood for something hot tonight, you should come see us play. Debut performance. I’ll make it real special for you.”

He decides to quit while he’s ahead and rises off the sand, suppressing a wince at the ache in his backside. As he dusts himself off, Josie looks up at him, dark eyes calculating. “I might be. In the mood, that is.”

“Excellent,” Dean says, winking as he starts to walk away. “I’ll see you tonight then. Don’t be late.”

*** 

“And where have  _ you _ been all afternoon?” Cas demands of his brother, still feeling disgruntled after watching Dean flirt with that underdressed, over-manicured woman at the beach earlier.

Gabe shrugs, flopping easily onto the foot of Cas’ bed. “Went for a walk.”

“Please.” Cas stops halfway through buttoning up his good shirt, the one he tries to save for performances. “You never engage in physical activity if you can possibly help it. You were avoiding me.”

“Oh?” Gabe, already dressed for the evening, squints down at his fingernails, inspecting them for non-existent specks of dirt. “And why would I do such a thing, Cassie?”

“I have a theory about that,” Cas says, doing up his last button and tucking his shirt into his slacks. “I think you have something to do with my roommate assignment.”

“I’m sure I don’t know what you’re talking about.”

“Your smirk says you do.”

Gabe exhales a world-weary sigh. “Cassie, you wound me. You have no trust whatsoever in your own brother.”

Deciding the time has arrived for drastic measures, Cas steps forward and pulls at the lobe of Gabe’s ear, hard.

“Owowowow  _ fine _ . After you two lovebirds fell asleep on top of each other, Charlie and I may have snuck Adler’s precious ledger from beside his bunk and made a few… adjustments to rooming arrangements.”

“I despise you,” Cas says, walking into the adjacent bathroom to look at himself in the mirror while he ties his bowtie.

“You do  _ not _ . You have definitely got the hots for this guy,” Gabe says, flinging himself onto Cas’ bed and bouncing up and down a few times on the mattress. “Although, if you two dance the horizontal tango in here, you might want to try the other bed. This one squeaks.”

Cas growls low in his throat, but makes no other response. The smooth, silky material of the bowtie slips from his hand, and he curses under his breath as he sets about retying it.

“Speaking of lover boy, where is he? Shouldn’t he be getting dressed?”

“I’m not his keeper,” Cas says, as carelessly as he can manage.

Of course, he should have known better than to think he could fool his own brother.

“You two have a tiff?” Gabe asks shrewdly, sitting up. “I did see him cozying up to Josie Knight in the lobby earlier. Redheaded mantis type, sex on legs, looks like she eats god-fearing folk for breakfast? Anything to do with that?”

The fabric of Cas’ bowtie slips through his fingers yet again. “How do you already know the names of everyone in the hotel?”

Gabe shrugs. “Not everyone. Just her. She’s famous. Heiress to the Knight Oil and Flammables fortune.”

Cas folds the ends of his tie so clumsily that the bow fails to materialize yet again. In a fit of frustration, he tugs at the fabric, hard, and it makes a complaining noise that sounds distressingly like a rip.

“Just let me tie the damn thing for you,” Gabe says, his tone a little softer than before. He walks up and takes hold of the tie, twisting and folding it in sure motions that produce a perfect bow in no time. Finished with that job, he claps both hands on Cas’ shoulders and looks at him with uncharacteristic seriousness. “You really like the guy.”

Cas shrugs uncomfortably, turning away to comb a bit of pomade into his hair in a futile effort to make it lay flat. “He’s here to snag himself an heiress and strike it rich, and he seems to have succeeded already. Good for him.”

Before Gabe can respond, the door opens, and Dean blows in like one of the famous Florida hurricanes.

“Fuck, I’m so goddamned late,” he mumbles, starting to undo the buttons on his casual linen shirt before the door has even slammed shut behind him. “Fucking Garth and Lee and their damned card games.”

“…aaaand that’s my cue to leave,” Gabe says, smirking at Cas as he passes behind Dean’s back. Cas rolls his eyes at him, then contemplates the distressing and alluring view of Dean slipping out of his shirt and starting to undo his belt.

Dean's chest is covered in the most alluring freckles, and Cas feels his face grow hot. It’s a good thing he’s already dressed. He was going to relieve himself before he left to go downstairs for the performance, but he can go do that at one of the public facilities. He just needs to retrieve his suit jacket from the armoire, and then he can leave. 

Except he’s so determined to walk fast and look absolutely anywhere but at Dean, he notices too late that Dean has moved right into his path. They collide, hard enough that Cas’ breath leaves him with an audible  _ whoosh _ .

“I’m so sorry,” he mumbles, “I wasn’t looking where I was going, I—”

He looks up. Dean’s face is inches away from his own, eyes wide with surprise. One of Dean’s hands has come up to rub at his own bare shoulder, where it crashed into Cas’ chest seconds ago, but Dean doesn’t seem focused on the motion. Instead, he’s staring at the lower half of Cas’ face. His mouth, to be exact. Cas might still have been able to extricate himself from this extremely compromising position, but then Dean does a disastrous thing. 

He licks his lips.

Cas is lost. He moves in, pressing his mouth against Dean’s, and the rasp of Dean’s unshaven, prickly jaw against his own smooth flesh is the stuff of poetry. With a low, pleased sound, Dean’s hand comes to rest against Cas’ lower back, pulling him in. Dean’s mouth opens, and Cas slides his tongue inside, an involuntary moan escaping him. Heat builds rapidly in Cas’ abdomen as he steps closer still, and—

Dean steps back.

He looks distinctly ruffled, cheeks flushed and eyes dark. “I, um. I’d better get dressed, Cas. I’ll see you downstairs. And, um, you know. Break a leg.”

“You too,” Cas mutters automatically, a sinking feeling in his chest. He tries to catch Dean’s eye, but Dean is already heading for the bathroom, shoulders hunched and face turned away.

Cas barely remembers to grab his suit jacket on his way out the door.

*** 

The Coronado’s nightclub is just as ostentatious as the rest of the place. Deep red, velvet curtains frame each entrance, and a sea of large, mirrored balls dangles from the ceiling, casting jumpy patterns of light and shadow on the mass of people below. The room itself is about five times the size of Dean’s apartment, and half of it is taken up by dozens of little tables. The other half, the one closest to the stage, is a dance floor. There’s still five minutes to go until the performance, so no one’s dancing yet, but plenty of people are sitting at or lingering near the tables, producing a constant, cricket-like susurrus of conversation.

Dean’s still a little out of breath from running late after that card game and, maybe, if he’s entirely honest, from that  _ kiss _ . It shouldn’t have knocked him off balance the way it did. A kiss was what he’d been trying for with Cas, wasn’t it? He should be happy. 

But as soon as their lips met, Dean knew he wasn’t going to want to keep it to just the one kiss. 

He’d wanted to blow off the entire performance, stay right where he was and explore every inch of Cas. More disastrously, he’d wanted to curl up in bed with Cas after, wanted to wake to see those fathomless blue eyes gazing at him with warmth and affection.

But that is a place where his head, and his heart, are not allowed to go. 

He forces himself instead to concentrate on the memory of Josie’s hand on his arm as they talked in the lobby earlier, and on adjusting the height of the microphone stand in front of him. He’s already adjusted it twice and knows perfectly well that the microphone is exactly where it needs to be, but keeping his hands busy helps stop his thoughts from straying. 

Behind him, the members of the band are taking their seats and tuning their instruments. As though drawn by a magnet, Dean’s eyes wander to Cas, who is frowning down at each string on his bass fiddle as he tunes it. Dean likes to think the frown is one of concentration, rather than anger or frustration at Dean’s abrupt dismissal.

On the spur of the moment, Dean decides that the entire thing is really Cas’ fault. He simply had to choose the absolute worst time for a kiss. Not only was Dean late to get ready for the performance, but his plan to find an eligible heiress was already going better than he ever expected. It simply wouldn’t be right to go around kissing handsome, charming men in his hotel room when he’s also trying to seduce the richest woman west of the Mississippi.

Realizing he’s been staring in Cas’ direction for much longer than would be considered acceptable in any setting, Dean moves to brush a non-existent speck of dirt off his performance suit. While all the other band members are dressed in black — either black suits or sequined dresses in glittering ebony, with plunging necklines — he and Donna are in matching white tails and waistcoats over black pants. Donna steps up next to him now, looking every inch the Dapper Donna persona with her immaculately tailored suit and gleaming bowtie, her flowing blonde locks pinned up and slicked back to make them appear more masculine.

“You ready, kiddo?” she asks, bumping Dean’s arm. He pushes down any lingering bit of nerves and dials up the wattage of his smile, until he lands firmly in performance territory.

“You know me, sweetheart,” he grins. “I’m always ready to go.”

Donna scoffs, then steps up to the microphone, flipping the switch to turn it on. “Good evening, ladies and gents,” she booms, and the audience falls mostly silent. “I’m Dapper Donna, and this is my orchestra.” She sweeps a hand around and behind her to indicate the semi-circle of musicians, who nod their acknowledgement. “We’re here to show you a good time tonight.” Polite applause erupts, and Donna waits, smiling demurely, until it subsides.

“My good friend Dean Winchester here—” She claps a hand on Dean’s shoulder, forcefully enough that Dean has to suppress a flinch and remind himself not to let his lips curve down or his teeth stop showing. “He’s a big name up in Chicago, where we hail from.” A blatant lie, but Dean lends it credence with an ostentatious wink. “And he and I thought we’d start things off tonight by treating y’all to our signature number. It’s called ‘Masculine Women, Feminine Men.’”

A mostly pleased, anticipatory rumble runs through the audience. The song’s been around for a few years now, performed by several different bands, and has gained a bit of a following. That said, Dean doubts most people in the audience tonight have seen it performed the way he has: by men dressed up in high heels, nylon stockings and low-cut dresses, at South Side drag balls. Once or twice, Dean was even the one performing, though he doesn’t generally advertise that fact.

With his stage grin firmly in place now, he rolls his shoulders, readying himself for a much safer, less raunchy rendition. Donna turns around to count in the orchestra, and the fast-paced, carefree tune starts up. Right on cue, Dean launches into the vocals, letting his low, rumbling baritone wash through and out of him.

_ Girls were girls and boys were boys when I was a tot _

_ Now we don't know who is who or even what’s what _

_ Knickers and trousers, baggy and wide _

_ Nobody knows who's walking inside _

He keeps his voice light and easy, letting everyone in the audience take from the song whatever they like. They want to complain about the immoral blurring of the sexes in the modern age? Let them do that (so long as it ain’t in Dean’s hearing). They want to celebrate the freedom of changing fashions? Even better.

Dean looks out at the audience, making sure to catch a few eyes and waggle his eyebrows suggestively at the females. Seamlessly, he steps aside to let Donna join him at the microphone when the chorus sets up, and they belt it out together:

_ Masculine women, feminine men _

_ which is the rooster, which is the hen _

_ It's hard to tell 'em apart today _

He steps back then, letting Donna take the opening lines of the second verse.

_ And say _

_ Sister is busy learning to shave _

_ Brother just loves his permanent wave _

_ It's hard to tell 'em apart today _

The lyrics flow past Dean’s ear, claiming just enough of his attention to make sure he doesn’t miss his next cue, even as he searches the crowd for a flash of red hair.

He finds it soon enough, at one of the tables that adjoin the dance floor. Josie is sitting with an older man. She’d said she was staying at the hotel with her father, who’s taking time away from the business for his health, so her companion is likely to be Mr. Knight Oil himself. Despite his elegantly cut suit and wavy silver hair, he looks frail, his skin liver-spotted and papery even from a distance — not exactly the picture of an imposing captain of industry.

Josie, on the other hand, is stunning. She’s wearing a floor-length gown, the navy silk looking beautiful against the vivid red of her hair and the pale tint of her skin. There’s a slit up the side of the gown that leaves Dean with an excellent view of one of those shapely legs he admired at the beach earlier. He would almost swear that leg isn’t encased in nylon, which is fairly scandalous, but he supposes the filthy rich can get away with a bit of scandal.

He and Donna finish out the song, cheerful and easy, and Dean bows at the resulting applause. It’s hardly thunderous, but definitely better than polite now. They’re starting to win people over. A few have even started to migrate to the dance floor. Dean turns to face Donna, who is having a quick, whispered conversation with the band to remind everyone what the next number is going to be.

Feeling a prickle at the back of his neck, Dean turns to find blue eyes fixed on him. Cas is next to Gabe, off at the left-hand side of the stage, cocking his head at Donna as though intent on her words, but his gaze never leaves Dean’s face. There’s a question in the way Cas is looking at him. Dean can’t begin to guess at what his answer would be, so he turns away, back to the microphone.

He glances at Donna, and nods to give her the go-ahead. Donna counts in the musicians, and a slow tune starts up, less jazzy and pretty heavy on the strings. A few people in the audience start taking their partners’ hands and heading for the dance floor. Dean takes a deep breath and begins to sing.

_ I wanna be loved by you, just you _

_ And nobody else but you _

As if on cue, Josie looks up from where she’d been in conversation with her table companion, and faces the stage. She’s holding a lit cigarette, lips wrapping around it as she takes a drag and meets Dean’s eyes. The gesture seems particularly suggestive in view of the lines Dean is singing now.

_ I wanna be kissed by you _

_ Just you, nobody else but you _

_ I wanna be loved by you _

_ Alone _

Yet, he can’t focus on the way Josie puckers her lips to blow out an elegant cloud of smoke. Not when other images keep intruding: being alone with Cas in their room, solid chest pressed against his; tasting those plush lips, that firm jaw under his fingers…

Dean can’t help it. His eyes leave Josie’s and slide over to the side of the stage, where Cas stands next to his bass fiddle, plucking the strings hard enough to break them, his expression stony. Dean almost misses his cue, but remembers just in time to keep going with the next few lines.

_ I couldn't aspire _

_ To anything higher _

_ Than to fill the desire to _

_ Make you my own _

Cas’ eyes meet Dean’s and widen minutely, something about his closed-off expression shifting as his fingers slow on the strings of his bass. Abruptly, Dean realizes why.

He’s turned his back to the room.

Probably for no more than a moment or two, but it’s an amateur faux pas. Quickly, he pivots back to Josie, who’s still looking his way, one eyebrow raised. He gives her a slow, lascivious smile, and she smiles back, seeming appeased.

After that, Dean makes sure to keep his eyes off Cas and firmly on the audience, all the while giving Josie an extra share of his attention.

It’s a delicate balancing act, and when Josie and her companion rise and leave the club a few songs later, Dean heaves a quiet sigh of relief.

He may have a problem.

**Notes for the Chapter:**

> Next week: Gabe and Charlie continue to scheme. Josie has a proposition for Dean. Cas reveals the secrets of his past.


	3. Chapter 3

**Notes for the Chapter:**

> The song in this chapter, "You'd Be Surprised", is a real song from the period. When I found it, I knew this fic was meant to be, because it's *obviously* about Cas. Here's [a recording](https://www.youtube.com/watch?v=6IFM5wWCMOo) from 1920. And yes, the song was originally performed by a man. Just to add the cherry on top, I found out later that Marilyn Monroe has [also recorded a version](https://www.youtube.com/watch?v=YR9T0sH1xH4).
> 
> But enough of this, because I'm mostly here to SQUEAL about the incredible, amazing, gorgeous art that the immensely talented [k6034](https://k6034.tumblr.com) created for this chapter. I haven't stopped staring at it in days. Please [give her some love](https://k6034.tumblr.com)!

Cas is seething.

He makes his escape from the stage before anyone can object, paying no mind to Gabe’s raised eyebrow, Charlie’s attempt to invite him to some sort of after-party, or whatever Dean may be doing, because Cas certainly isn’t looking at _him_.

As he’s waiting for the elevator to arrive, he taps his foot impatiently, then proceeds to grumble the entire ride up, while the pimpled teenage operator shoots him slightly alarmed glances. Once Cas has finally been deposited on the third floor, he stalks to his room, slamming the door much too loudly.

Who in the world does Dean Winchester think he is? Returning Cas’ kiss, only to reject him immediately after. Spending most of the damnable performance making bedroom eyes at that red-haired hussy, only to then flirt with Cas in full view of an entire ballroom’s worth of people. Cas may be a lot of things, but he is not a pushover, and he will _not_ be led on. 

If Dean wants someone to kiss and then discard once he’s secured his engagement to one of the country’s richest women, he can damn well look elsewhere, and that’s that. 

In fact, Cas is determined to go to bed without delay and have a good night’s sleep that will definitely, absolutely not be disturbed by dreams of Dean Winchester.

He holds on to this conviction with a white-knuckled grip as he brushes his teeth — hard enough that his toothbrush bends a little — performs a cursory wash under his armpits, and pulls on his striped pajamas. He only owns one pair now, out of the near-dozen he used to have. The fabric is a sturdy cotton blend, very unlike the sleek satin he was once accustomed to wearing. But this pair seemed the most sensible one to keep, and it’s served him for months now without developing a tear. A good choice, all things considered.

A good choice is exactly what his extremely brief involvement with Dean _hasn’t_ been. Dean is here for the express purpose of finding a rich heiress to marry. Cas is no longer rich, nor is he a prospect for marriage to another man. 

He will act composed and civil towards Dean for the rest of their time at the resort, and then they will go their separate ways. Perhaps he should ask to room with someone else, but all things being equal, he would rather not let Dean know that he’s even the slightest bit affected by their sleeping arrangements.

By the time Cas turns out the light, he’s reasonably pleased with himself for stopping his unfortunate infatuation with Dean Winchester in its tracks.

But sleep is a long time coming. 

Cas is still wide awake two hours later, when the door inches open and the soft glow from the wall fixtures along the corridor inches across his bedspread. Dean sneaks into the room on tiptoe, but bumps against the door halfway through, causing it to swing wide open. Cas squeezes his eyes shut against the sudden brightness, and Dean freezes in the doorframe.

“Sorry, man. Didn’t mean to wake you.”

“I wasn’t sleeping,” Cas growls, sitting up.

“Oh.” Dean closes the door behind him. “In that case, mind if I turn on the light?”

“Fine.”

Dean flicks the switch, and the ceiling lamp flares to life. Grumbling, Cas flops face-first onto his pillow to shield his eyes. Dean chuckles, and Cas, more annoyed than ever, squints sideways at him. “Can I help you?”

Dean shakes his head, a fond smile now etched on his face. Cas notices that the collar of his shirt is sticking up on one side. He could swear there’s a lipstick stain on it, too. Evidently, Dean and his heiress have made the most of their night. Cas rises off his pillow and punches it, working out his frustrations under the guise of getting more comfortable.

Dean closes the bathroom door, and the sound of running water starts up. Cas is once again determined to go back to sleep, but his renewed annoyance and the bright glare of the overhead bulb are making it extremely challenging.

As a result, he’s still awake when Dean emerges, pink-cheeked, wearing pajama pants and a sleeveless white undershirt that does absolutely nothing to conceal the constellation of freckles across his shoulders. Silently, but emphatically, Cas curses every single one of them.

He turns his face to the wall and closes his eyes, determined to get some sleep at last. The flick of the light switch sounds, and blissful darkness descends again. Next, Cas expects to hear the creak and shuffle of Dean getting into bed, but it doesn’t come. Instead, his _own_ bed dips, and the pale moonlight streaming through a gap in the curtains outlines Dean’s silhouette. 

He’s sitting mere inches away, one knee up on Cas’ mattress to face him fully. "Cas?"

He should tell Dean in no uncertain terms to go away and keep his sinful lips and beautiful hands and all his other body parts to himself. Instead, he merely grunts, which Dean seems to interpret as permission to keep talking.

“I wasn’t with… Josie, if that’s what you’re thinking. Just had some drinks with Charlie and the other girls from the band.”

“I don’t care,” Cas says, sounding petulant even to himself. But it’s too late to be mature now, so he rolls away, turning his back on Dean.

After a beat of silence, Dean says, “I know you’re mad at me. ‘Cause of, you know. The kiss. And how I behaved after.”

It’s an entirely accurate assessment of Cas’ state of mind, but he doesn’t say so. What he does do is roll back to face Dean, and he regrets it immediately. The moonlight puts Dean’s cheekbones into sharp relief, painting shadows across them and making him look almost unearthly.

“I know there’s no chance of anything serious between us,” Cas says. His heart aches with the admission, but it’s no less true for that small twinge of regret.

Dean exhales heavily through his nose. “Cas, it’s… not like I don’t want there to be, you know? I like you. A lot. I just wish…” He breaks off and looks away, face turned to the gap in the curtain. “I dunno what I wish. Maybe that I wasn’t poor? That I could take care of my ma without shackling myself to some snobby, arrogant rich girl?” Dean hangs his head. He looks tired. “Or maybe that _you_ weren’t. Poor, I mean. Or that I could think of some way to make a big success of myself.” He chuckles mirthlessly. “I’m not very bright, I guess.”

“I didn’t used to be poor.” The words are out of Cas’ mouth before he can call them back, pulled forth by the downward twist of Dean’s mouth, the way his shoulders slump. “Gabe and I are the sons of Charles Novak.”

“Oh.”

“Yes,” Cas agrees. “Oh.”

Everyone knows the story: Charles Novak, the famous industrialist who was accused of tax evasion, but left the country before he could be put on trial. The government froze his assets, leaving his sons in dire poverty.

“And you’re still here,” Dean says. There’s something proud, almost awed, in his voice. “You and Gabe are using the skills you’ve got and earning your own keep. Good for you, Cas.”

“Thank you, Dean,” Cas croaks. Every nerve in his body strains to sit up and get closer. He resists the impulse. “But the fact remains that I’m poor as dirt _now_. And I understand that means I’ll never be an attractive romantic prospect — not for you, not for anyone. So I think it’s best if we keep our distance until the band's engagement here is over.”

The words scrape at his throat, and he despises the way Dean’s expression tightens, but it can’t be helped. This is the best possible course of action for all concerned.

Dean nods and slips off the bed. Cas closes his eyes and fists his hands under the sheets, not wanting to be tempted any more than he already has been tonight. 

But before Dean steps away, Cas feels a soft, fleeting touch on his arm. 

Cas doesn’t pull away, but he doesn’t respond either.

By the time he finally falls asleep, the first tendrils of morning sunlight are creeping across the floor.

*** 

The band’s rooms are on the third floor of the hotel, and they’re fine. Serviceable. The accommodations are small, but clean, and the pipes are never short of hot water.

But here on the top floor, it’s a different world. As soon as Dean steps off the elevator, his feet sink into Persian carpeting, deep and soft as a spring meadow. Framed portraits of noted Floridians line the walls, and a genuine Faberge egg sits on a side table Dean passes on his way down the hall.

His palms are sweating a little. To distract himself from his nerves, he worries at the piece of paper clutched in his right hand.

He spent a good part of the day looking for Josie — partly because he wanted to build on their acquaintance, partly to have an excuse to stay out of Cas’ way. It wouldn’t do to dwell on how Dean woke up this morning to the sight of Cas' sleep-soft face, and how he wanted nothing more than to run his fingers through the dark, messy hair spilling onto Cas’ pillow.

He never found Josie, and in the end decided to take a solitary walk into town. On returning to the hotel, a message was waiting for him at the front desk:

_Come to my suite, 1042, after tonight’s performance. I’ll be expecting you. – J_

So here he is, feeling thoroughly out of place as he makes his way down the ostentatious corridor, with its gold-flecked wallpaper and heavy, mahogany furniture.

When he arrives at the door of 1042, his knock is almost immediately answered by a stiff, bland-faced lackey in a tailcoat. Figures that Josie Knight doesn’t open her own door, even in a hotel room.

“I’m Dean Win—” he starts, but the lackey cuts him off with a disdainful look.

“Miss Knight is expecting you.” He steps aside to usher Dean into the suite, and it’s easily the ritziest place Dean’s ever been. The chandelier in the middle of the room looks like a replica of the one in the lobby. There’s a fireplace against one wall — a rather ridiculous feature in the south of Florida, Dean can’t help thinking. Comfortably upholstered, high-backed chairs surround a gleaming table by the fire, and a piano sits in pride of place next to the large French windows. It’s dark outside now, of course, but Dean would bet anything the windows have a stunning view of the sea.

In the far corner is a four-seater couch, each seat back adorned with an intricately flower-patterned antimacassar to prevent the cushions from being stained by pomade.

“Wait here,” the lackey says curtly, not so much as asking Dean to sit down. Instead, he moves silently through a doorway by the piano, and holds a murmured conversation with someone in the next room.

A moment later, Josie emerges, sans lackey. She’s wearing a purple silk gown that flares out at the bottom and, Dean notices when she turns to pick up her cigarette case from a marble side table, plunges deeply in the back, leaving a wide expanse of smooth, pale skin on full display. 

“Thank you for coming, Dean,” Josie says, when she turns to face him again. Her predatory smile suggests the back-turning maneuver was entirely intentional.

“My pleasure,” Dean says, as steadily as he can, considering the roiling mix of anticipation and nerves in his gut. “Mind if I sit?”

“By all means, join me,” Josie says, but to Dean’s surprise, she points to the chairs surrounding the table, as opposed to the much more amicable venue of the couch. Still, Dean complies. “Care for a drink?” she asks, making her way to a bar cart that sits next to the fireplace. Evidently, Prohibition doesn’t have the force of law where the very rich are concerned.

“Sure,” Dean says easily. “Whiskey neat. But ain’t that a job for your lackey?” He inclines his head at the doorway where said lackey disappeared.

“Normally, yes,” Josie says, filling two crystal tumblers from a decanter of amber liquid, then replacing the stopper with a soft _clink_ of glass. “But I asked him not to disturb us, so he won’t. He’s very… discreet.”

She glides over to where Dean has taken a seat, long, painted nails curled around the delicately patterned crystal. Setting one tumbler down in front of Dean, she surprises him again by choosing the chair opposite his own, all the way across the table. It’s not a terribly large table, but it’s large enough that they won’t be able to so much as play footsie under it.

Dean opens his mouth to speak, to try some kind of line that will cut through the strange formality of the situation, but Josie cuts him off. “I have a proposition for you, Dean.”

The blunt statement throws Dean off balance, but he recovers quickly, painting on a lascivious grin. “I’m at your service, sweetheart.”

Josie clinks a fingernail against her glass, one side of her mouth curving up. “It’s not that kind of proposition.” She tilts her head ever so slightly, considering. “Well, I suppose it may be, eventually. But not just yet.” She leans forward, fixing Dean with a calculating stare. “For now, this is strictly business.”

No witty response suggests itself, so Dean says, “Oh?” and steadies himself with a sip of his drink. It’s easily the best whiskey he’s ever tasted — smooth, warm and mellow.

Josie nods, any trace of a smile gone from her face now. “My father isn’t well, Dean. He hasn’t been for years.” She regards him steadily, her glass sitting untouched in front of her. “I’ve been running things behind the scenes, keeping the company afloat, with my father not much more than a figurehead who poses for pictures. But his illness is progressing quickly.” She grimaces, more inconvenience than genuine regret. “He’s not long for this world. I have every intention of continuing to run Knight Oil, but the shareholders won’t accept a woman at the helm.” She leans forward, a hungry gleam in her eye. “What I need, Dean, is another figurehead.”

The pleasant whiskey warmth seeps out of Dean’s veins with startling speed. “You’re talking about _me_.”

“Naturally,” Josie says primly, taking a small sip of her drink. “I need a man — to be entirely clear, a husband — who won’t interfere with my running of the business.” She smiles, big enough to show off the glint of her canines. “Someone who’ll look pretty in pictures and make nice with the shareholders, but won’t otherwise get in my way.”

Dean picks up his tumbler and opens his throat, downing the rest of his drink in one big swallow. The heat of it trickles through him again, but this time, there’s no pleasure in it. “What’s in it for me?”

“Oh, I think you know that very well,” Josie sneers. “All the trappings of a rich life. The clothes, the cars, the houses… whatever your heart desires.” She brings her hand to her mouth, running a thumb suggestively along her full bottom lip. “And I do believe we’ll be expected to produce an heir in time.”

“Would I—” Dean swallows, trying to think how to put this without giving too much of himself away. Josie doesn’t seem the sort of person who should be handed weapons. “Would I have any money of my own? To use as I see fit?”

Josie smiles, secure in her victory. “Of course. You‘ll be free to incur whatever expenses you like, as long as they’re unrelated to Knight Oil and the running of the business.”

Dean’s mind is racing, torn. This offer is everything he’s ever wanted, presented to him on a silver platter: a way to take care of his ma. An easy life of pleasure and leisure for them both.

He tries to picture himself as a trophy on the arm of one of America’s richest women. Day in and day out, smiling and posing for pictures, only to come home to a house where he knows he isn’t loved, or even particularly wanted beyond his usefulness.

Another set of images intrudes on his thoughts: dark hair, painted silver by the moonlight. A warm body, curled up against his leg. Eyes the color of a sun-drenched ocean, staring back at him across the concert stage.

“Can I think about it?” he asks, steady as he can make it sound.

Josie nods, curtly. “My father and I will be departing on our private yacht the day after tomorrow. You have until then.”

Realizing that he’s being dismissed, Dean gets up and makes his way to the exit. When he returns to his own room, it’s to find that Cas has already fallen asleep, and Dean thanks his lucky stars for small blessings. 

*** 

The next morning finds Dean and Charlie heading into town for a lunch date.

Waking up in the same room with Cas again was awkward at best and torture at worst, Dean’s eyes drawn like magnets to the flutter of Cas’ dark lashes, the wrinkle of his nose as he slid from sleep to consciousness.

His interactions with Cas have been perfectly pleasant and polite since their talk, but there’s a distance to them now, a formality that Dean hates to see, especially with thoughts of Josie’s proposal playing on a loop in his head.

At his wits’ end, he finally went to Charlie’s room mid-morning, telling her all about Josie’s offer — as well as his inconvenient and extremely ill-timed attraction to Cas.

“What you need,” Charlie had declared firmly, “is a walk to clear your head, and a full stomach.”

So here they are, making their way across the lobby, on their way to look for a beachside hot dog stand.

“I’ve just felt so off my game over the whole thing,” Dean says, as they pass a pair of tall ladders, atop which wobble two unfortunate hotel employees. “I barely know the guy. Why should he have that kind of effect on me?”

Under the anxious direction of a man with the fatuous air of a low-level manager, the employees are busy affixing a blood-red banner to the rear wall. It reads, in impressive gold letters:

_FRIENDS OF ITALIAN OPERA_

_10th Annual Conference_

_Welcome, Delegates!_

“Because you’re in love with him, you sap,” Charlie answers cheerfully.

Dean is so busy gaping at her in disbelief, he runs straight into a solid wall of muscle.

“Watch where you’re going, eh?” the wall snarls at him.

Dean takes a step back, frowning up at the very definition of a goon face: boxer’s nose, broken at least two different times, small, piggy eyes, close-shaved head and a cauliflower ear. Dean wants to come back with a sharp retort, but he feels Charlie’s steadying hand on his shoulder. Subtly, she nods to Dean’s left, where a guy who has to be the goon’s identical twin is standing, not ten feet away.

What’s worse, the two goons frame a man in a pinstriped suit, carefully tailored at ankle height. He’s got a heavy wool coat draped over his shoulders, even in the Florida heat, and his feet are encased in a pair of dazzlingly white spats. Despite his relatively small stature, there’s an air of effortless menace about this man.

Dean’s spent all his life in Chicago, and years of it performing in speakeasies and nightclubs around the city. He’d recognize Spats Crowley anywhere.

Heart beating faster, Dean nods a polite apology and lets Charlie pull him along, out the front door and across the porch. “What in fucking blazes is Spats Crowley doing here?” he hisses at Charlie.

Behind her, a man in one of the porch chairs sits up a little straighter. Dean catches his eye for the briefest moment. He’s burly, broad-shouldered and wearing a newsboy cap. The stranger frowns up at Dean, considering, but Dean has no time to process that reaction, because Charlie still has a firm grip on his sleeve. Unless he wants to break his neck going down the porch stairs, he’ll have to start paying attention to where he’s going.

“I don’t know, but Donna told me this place is popular with the Chicago mob. It’s why they like to book Chicago bands.” Charlie finally lets go of his sleeve when they reach the path that leads to the main road. “Besides,” she adds, with a wicked grin, “I believe we were talking about your love life.”

“There’s nothing to talk about,” Dean says, waiting for a sputtering bus of happy vacationers to pass before he steps into the road. “I’m not in love. I don’t fall in love.”

Charlie snorts. They’ve reached the opposite sidewalk and set out north along the palm tree-lined promenade, making for the center of town. “Tell it to the other one, Winchester. You’ve been making gooey eyes at that boy ever since you first laid eyes on him.”

Dean stuffs his hands into the pockets of his suit pants and hunches his shoulders. “So what if I have? Even if we had the right set of parts between us to get married, we’re a couple of penniless musicians without a prospect in the world. We’d be miserable and poor and end up hating each other’s guts.” He shakes his head mulishly. “Josie is the smart choice.”

Charlie aims a rather painful punch at Dean’s shoulder, and he rubs at the sore spot, glaring. “What?”

“You’re kidding yourself,” she says, eyes blazing, “if you think you’ll be happy yoked for life to some vapid rich girl who keeps you around for nothing but your perky nipples. Sometimes, the _heart_ choice is the smart choice.”

Dean opens his mouth to retort, but Charlie heads him off with a poke that hits, unerringly, in the exact same spot as her earlier punch. “And why d’you need to be rich, anyway? You’ve done alright for yourself so far, with that pretty face and that panty-dropping voice of yours.”

“Sure, great,” Dean growls, scowling at Charlie. An alarmed-looking nanny pulls her privileged, sailor-suited charges aside to let him pass. “And you know what? Neither one of those is gonna last. I’ve got maybe another decade of good looks left, if I’m lucky, and once those are gone, no one’ll give a damn about my voice, or talent, or any of it.”

“So you’re throwing yourself at the rich girl who doesn’t give a damn about _you_? Really? That’s your solution?” Charlie’s voice is rising now, and more than a few passersby are staring as the two of them make their stomping, disgruntled way past the first few shops in town.

“If you can think of a better way to set me and my ma up for life, I’d like to hear it.”

Charlie huffs, a bone-deep exhale that’s sufficiently dramatic to compete with the sound of waves whooshing against the beach to their right. “There’s _always_ a way. And besides, you’d be miserable married to that vamp.”

“Maybe,” Dean admits, more quietly. “But it doesn’t matter.”

Charlie stops and turns to face him, forcing the surrounding crowd of vacationers to flow around them. “So what? You’re gonna pop the question and ride her coattails into the sunset?”

“That’s the idea,” Dean says, staring determinedly at a gull pecking at an abandoned food wrapper ten feet down the promenade. 

When he finally meets Charlie’s eyes, it’s to find her gaping at him in naked disbelief. “You’re a prize idiot, you know that?”

“It’s been said,” Dean mumbles, doing his best to ignore the heavy weight on his chest as he strides past Charlie and heads further into town.

*** 

At the performance that night, Cas tries his hardest to keep his eyes off Dean. No matter the time of day, Dean is a walking temptation, but never more so than when he’s in a well-pressed suit, commanding the stage with his resonant voice and blinding smile.

Cas stares down at his fingers, focused on the way they move across the strings of the bass fiddle. But he can’t help listening to the music, and he can’t help the tingle under his skin as Dean’s voice wraps itself around the lines of one of the band’s signature numbers.

_He's not so good in a crowd but when you get him alone_

_You'd be surprised_

_He isn't much at a dance but then when he takes you home_

_You'd be surprised_

Despite Cas’ best intentions, Dean’s voice is a magnet, and Cas may as well be composed of iron filings. His eyes lift, purely of their own volition, to center stage, where Dean is bending over his microphone, caressing it suggestively as he winks at the females in the audience. The song is, ostensibly, about a woman defending her lover, but the fact remains: it’s an ode to a man, sung by someone who has rarely left Cas’ thoughts since their first meeting.

Cas despises himself a little for wishing Dean would turn around, like he did that first night, and serenade _him_ with the words of the song.

_He doesn't look like much of a lover_

_But don't judge a book by its cover_

_He's got the face of an angel_

_But there's a devil in his eye_

Cas sighs and resolves to shift his attention back to his brother, who has been acting extremely suspicious all evening. Gabe, as always, is playing next to Cas, whereas Charlie is almost all the way at the other end of the stage. Yet, Gabe has dashed over to her seat after each song so far, bending over to whisper in her ear. Every time, Charlie giggles and practically bounces with excitement at whatever Gabe is telling her, which Cas finds rather worrying. 

Finally, having met his limit for the night, Cas tugs at Gabe’s sleeve as soon as “You’d Be Surprised” wraps up. “What are you two scheming about this time?”

Gabe raises a single brow and flicks Cas’ cheek, prompting Cas to let go of his brother with a muffled curse. “Nothing that needs concern you, baby bro. Not everything is about you, you know.” Gabe grins lasciviously. “Maybe the fair Charlie and I have a hot date after this.”

Cas snorts. “I know for a fact that Charlie is interested in women in general, and Dorothy in particular. So pull the other one.”

“If you say so,” Gabe responds, still grinning.

Cas was undoubtedly going to think of an eloquent retort, but loses his chance when Donna turns back to count in the band for the next number. After that song is done, Gabe once again makes a beeline for Charlie’s seat, and for the rest of the night’s performance, Cas can’t shake off a feeling of foreboding.

They wrap up the last two songs, followed by enthusiastic applause from the dance floor and the tables in the back. As soon as Cas’ bass fiddle is back in its instrument case, he feels Gabe’s hand on his sleeve, pulling him backstage. 

“Listen, baby bro, Charlie passed me this note for you.” Gabe presses a small, crumpled square of paper into Cas’ hand. Cas looks down at it, frowning, and Gabe nudges him. “Aren’t you gonna read it?”

“Certainly not with _you_ around.”

Gabe sighs, world-weary. “Fine. I’ll turn my back.” He does so, with a dramatic pivot on his heel, and Cas decides not to pick this particular fight. He unfolds the paper and looks down at a few lines in blocky, messy script:

_Cas,_

_I need to talk to you. Can you meet me after the performance? There’s a roadhouse half a mile down the coastal highway to the south. They don’t ask a lot of questions, and they’ll serve you drinks if you ask for “coffin varnish.” I’ll wait for you there. Please come._

_Dean_

Cas frowns down at the note as he reads and re-reads it, his lips silently shaping themselves around the phrase “coffin varnish.” He’s so absorbed that he doesn’t notice Gabe is reading the note over his shoulder until his brother asks, “Well? Are you going? I think you should go.”

“For fuck’s sake, Gabe.” Cas aims a sharp kick back at Gabe’s shin. It connects, resulting in a satisfying hop and a yelp. “That note is private. And give me some time to think, would you?”

“What’s there to think about?” Gabe asks, rubbing ruefully at his leg. “Your boy wants to see you. Go get ‘im.”

Cas hums, considering. “I suppose there’s no harm in going down there.” He looks down at his performance suit. “I should change back into the wool, though. I don’t want to have to pay to get this thing cleaned if I can help it.”

“Get over it, Cassie. You look great. And Dean’s already gone, see? Don’t wanna keep him waiting.” Gabe motions back to the stage and, sure enough, some of the band members are still packing up their instruments, but Dean is nowhere to be seen. “I’ll even take care of your fiddle for you.” Before Cas can so much as lodge a protest, Gabe has divested him of his fiddle case.

“Fine,” Cas concedes, then points a threatening finger at his brother. “But this had better not be one of yours and Charlie’s schemes.”

“Scout’s honor,” Gabe says, holding up his right hand in a two-fingered salute.

Cas squints at him, more suspicious than ever. “You were never a boy scout.”

“That’s all _you_ know,” Gabe says, even as he turns to walk back on stage. “I’m off for that hot date with Charlie. You get outta here, and misbehave if you think you can manage.”

Reluctantly amused, Cas turns away and makes for the back of the hotel, intent on finding the path that leads to the coastal highway. It turns out to branch off the path to the beach, and dead-ends at the road after about a quarter mile.

Cas has been walking along the highway for less than ten minutes when he spots a string of lights adorning a squat, wooden structure that clings precariously to the edge of a cliff. The sounds of cheerful Cuban music emanate from its general direction, beckoning him closer.

Next to the building, a set of stairs leads to a patio set slightly lower down the cliff. It’s strung with fairy lights on all four sides and ringed with lush, tropical growth, swaying palm fronds competing with the pop of deep-red canna lilies and orange milkweed.

Off to one side is a bandstand, where the Cuban musicians are giving it their all, strumming guitars, blowing trumpets and shaking maracas. The members of the band are dressed in ruffled white shirts, purple cummerbunds and black pants, their eyes covered with plain black blindfolds.

Cas wonders why on earth anyone would blindfold musicians, but he’s torn out of his thoughts by the sound of his name, shouted from the side of the patio that’s closest to the ocean. “Cas!”

He turns to find Dean seated at one of the tables, waving at him, a welcoming smile on his face. Cas’ heart performs a skip as he returns Dean’s smile and walks onto the patio, maneuvering around several dancing couples to get to where Dean is sitting.

It’s a small table, just big enough to fit a chair on either side. A purple orchid sits in a vase at the center, and as Cas takes his seat, he can’t help but notice how the two small tea lights on the table and the fairy lights above them cast Dean’s face in a soft, golden glow.

“Hello, Dean.”

“Hiya, Cas.” Dean holds up a squat glass filled with amber liquid. “Would you believe it? The coffin varnish they serve here ain’t half bad.” He motions back at the building by the highway. “They don’t do table service, so you gotta go inside to grab a drink. Want me to get you one?”

“Sure, let me just…” Cas reaches for his inside pocket, where he always keeps a few coins, but Dean is already up. 

He puts a hand on Cas’ wrist, arresting its movement. “It’s on me, man. Don’t worry about it.”

With an almost shy grin, Dean walks away, and Cas wonders more than ever why Dean asked him to come here tonight. Is it possible he’s given up on his plans for Josie? And if so, could there be a chance for something more between them?

As he waits, Cas amuses himself by watching the couples on the dance floor. With interest, he notes that one of the dancing pairs is comprised of two females.

Dean returns a minute later, clutching a glass filled almost to the brim. “How did you know to ask for ‘coffin varnish'?” Cas asks, as Dean sets down the drink in front of him.

“Oh, Charlie and I came here a couple nights ago. She’s got a talent for making friends everywhere she goes. Chatted up the owner’s daughter. Guess she figured we weren’t cops, so she let us in on a few things.” Dean shrugs, one corner of his lips ticking up. “We both got honest faces, I guess.”

Dean raises his glass, and Cas clinks his own against it. He takes a small sip, grimacing against the burn. “Definitely an acquired taste.”

Dean chuckles. “Guess so.” He takes a generous swallow from his own drink. “So, you wanted to see me?”

At that, the second sip slips down Cas’ windpipe, and he coughs and wheezes until Dean, looking concerned, walks around to his side of the table to slap him on the back. 

When Cas has regained the ability to draw breath, he croaks, “ _I_ wanted to see you? _You_ sent me a note, asking to meet me here.”

Dean blinks at him. “I never— No, wait, _you_ were the one who—” He breaks off as his eyes widen in apparent realization. “Charlie.”

Cas sighs, rubbing at his face. “I take it she passed you a note purporting to be from me?”

“She sure did.” Dean looks down at his glass, turning it between his hands. “I’m a moron. Should never’ve told her about how I was planning to marry Josie.”

Cas’ heart plummets to the flagstones at his feet. “You were?”

“Yeah. Shouldn’t have told Charlie _that_ , and shouldn’t have admitted that I’d probably be miserable, marrying for money. Like I said before, I’m not very bright.” Dean downs the rest of his drink. “If I was, I would’ve guessed she’d hatch some scheme to throw the two of us together instead.”

Cas’ heart rises back to its accustomed place, beating a frantic rhythm against his ribs. “Why would she want to… throw us together?”

Dean’s cheeks seem to gain just a hint of color, though it’s hard to tell in the soft light. He waves a dismissive hand, but doesn’t meet Cas’ eye. “Doesn’t matter. You want another?”

Cas has barely made a dent in his drink, so he shakes his head, and an awkward silence falls.

After a minute, Dean clears his throat. “You ever miss it? Being rich, I mean?”

Cas considers the question. “Sometimes. A lot of things were certainly easier. I never went hungry, and I was hardly ever cold. I miss riding, and skeet shooting with my friends.” He scratches at a small stain on the white tablecloth, because it’s easier than seeing the disdain, or worse, pity, in Dean’s expression. “Then again, those friends all disappeared rather quickly when the news came out about my father, so maybe they were never friends to begin with.”

When he finally does look up, Dean’s eyes are already on him. “Never knew anything but being poor myself,” Dean says, grimacing, as though the admission is somehow shameful. “We always struggled to keep our bellies full and a roof above our head, far back as I can remember. My little brother, Sam, he’s done better for himself, but he left the family to do it. Probably figured ma and I were keeping him from getting ahead in life.” Expression tight, he adds, “Had the right idea there, I guess.”

“I’m sure that’s not what he thought.” Gingerly, and buoyed by the faint buzz of bourbon coursing through him, Cas reaches out to pat Dean’s hand where it’s resting on the table. “What does he do?”

Dean’s face lights up at the question, and he launches into a clearly well-worn speech about his brother’s small-town law practice, his wife Eileen, and the two young children Dean got to see one time when he had a touring engagement in the area.

By the time they’ve exhausted the subject, Cas feels warm and content, and he finds himself leaning forward more and more, cursing the table that separates him from Dean and his plush, tempting lips.

As if lured by the thought, Dean leans forward too, his face now mere inches away. The Cuban band is playing an upbeat tango. “You know why they blindfold the musicians?” Dean asks, just loud enough to still be heard above the music.

“Why?”

“Supposedly, it’s to show how well they know their instruments. But the owner’s daughter told Charlie, the real reason is to show there’s no judgment. No one watching. Anyone can dance with anyone, and there ain’t a soul around to see.”

“Anyone?” Cas blinks hard, trying to break the spell of Dean’s closeness enough to form a full sentence. “I did see two women dancing together earlier, but are you saying…?”

_That two men could? That we could?_

Dean smiles, soft and fond, and holds out his hand, palm up. “You wanna dance, Cas?”

Cas _should_ say no. But the night is warm, the light is soft and Dean is very, very charming.

Feeling almost giddy, he takes Dean’s hand and lets himself be dragged into the small group of dancers. Dean pulls him in close, clasping his right hand in the traditional ballroom hold. His other hand rests on Cas’ hip, indicating that he’s going to lead. Dean’s steps are sure and practiced as he sweeps them across the floor to the sounds of a rousing foxtrot. Cas, on the other hand, stumbles a little as he tries to adjust to the unaccustomed female step pattern, but each time he does, Dean laughs, low and cheerful, and Cas figures that’s just fine.

He doesn’t know how much time passes this way, only that he’s feeling light and happy in a way he hasn’t felt since before his father fell from grace. Dean, loose, smiling and relaxed, fills every last one of his senses, and he barely even notices as the crowd around them thins out, the couples departing one by one, until there is no one else left.

The band sets up a new song, the melody vaguely familiar, but Cas can’t put his finger on quite what it is, too busy noticing the way the fairy lights are reflected in the green of Dean’s eyes as they sway slowly around the empty dance floor.

After a few more chords, Dean chuckles, recognition sparking on his face. He bends forward, whisper-singing in Cas’ ear.

_He's not so good in a crowd but when you get him alone_

_You'd be surprised_

_He isn't much at a dance but then when he takes you home_

_You'd be surprised_

Cas smiles, the upward tilt of his lips almost involuntary. He grips Dean’s hand a little tighter, and feels Dean’s lips against his cheek as they shape the words of the next few lines.

_He doesn't look like much of a lover_

_But don't judge a book by its cover_

_He's got the face of an angel_

_But there's a devil in his eye_

Dean’s lips keep moving until they’ve reached the corner of Cas’ mouth. His hand leaves Cas’ hip and glides up his arm, cupping the back of his neck. They’re pressed together now, all pretense of dancing abandoned, Dean’s warm, solid presence somehow comforting and intoxicating in equal measure.

“Dean, what are you doing?” Cas whispers against Dean’s lips, trying hard to call to mind all the reasons why he was supposed to keep his distance from Dean.

To his great distress, he manages it.

“This can’t… Dean, you’re going to marry Josie.” Dean steps back, expression unreadable. “Aren’t you?” Cas asks, voice quavering around the question he wants, and yet doesn’t want, Dean to answer.

Dean looks down at the dance floor between them, and Cas' hands ball into fists at his sides. The musicians finish their song and take off their blindfolds, struggling with various instrument cases as they put their things away. Cas is more interested in the struggle playing out on Dean’s face, wishing he knew how to turn the tide of battle in his favor.

“I thought I could do it, you know?” Dean says quietly, over the soft sound of waves crashing onto the beach below. “I thought, for my ma, I could give up on the idea of… of happiness, of love. I meant to.” He looks up, devastation written plainly in his expression. “Hell, I wanted to. But…”

Without his permission, Cas’ feet carry him closer to Dean. “But?”

Dean's expression softens, the smallest hint of hope sparking in his eyes. “Cas, do you want this? D’you want _me_?”

“It doesn’t matter what I want.” He reaches down to take Dean’s hand, entwining their fingers. “I’m still a man, and I’m still poor as dirt. None of that has changed.”

A muscle in Dean’s jaw ticks, but his voice is quiet, steady, when he says, “Just answer the question, Cas.”

“Of course I do,” Cas whispers, his throat tight. “That was never in doubt.”

“Then follow me.” Dean lets go of his hand and walks up the stairs that lead back to the highway, then on through the door into the dim interior of the roadhouse. A middle-aged woman stands behind the bar, wiping at a glass with a dusty rag.

“Phone?” Dean asks her.

“In the back,” she says, and returns to her task.

Dean heads for the black box along the far wall, digging in his pocket until he comes up with a handful of coins. Cas watches from a distance, not daring to speculate on what’s about to happen. “Operator? The Coronado. Room 1042.”

Dean waits, the receiver pressed to his ear, until a female voice sounds from the other end, faint and tinny. “Josie? It’s Dean.” He takes a deep breath, then says, “Listen, I just… wanted you to know that, the offer you made me? I just got a better one.” He makes sure to meet Cas’ eyes when he adds, “So I won’t be taking you up on yours.”

Silence on the other end, and then a dial tone. Dean hangs up the phone, looking equal parts confused and relieved. “Wow. Thought she’d chew me out. Get tearful, maybe. Not sure if I should be glad or insulted.”

Cas steps closer, hardly daring to believe his luck. He searches Dean’s face for any sign of regret or hesitation. “Dean, are you sure this is what you want?”

Dean’s answering smile is the perfect warmth of a summer evening, and the comfort of home after a long day. “What I want,” he says, “is for the two of us to get out of here.”

**END PART I**

**Notes for the Chapter:**

> Next week: Dean and Cas celebrate their newfound understanding. Dean gets another proposition. Cas discovers that Spats is staying at the hotel.


	4. Chapter 4

**Notes for the Chapter:**

> Today, we earn our "Explicit" rating! If that's not your thing, you can skip the first scene without missing anything in the way of major plot.

**PART II**

When Dean and Cas emerge from the roadhouse’s interior, the porch below is utterly deserted, no sign of musicians or dancers remaining.

Dean looks over his shoulder to find Cas right behind him, his face lit up with a wide, dazzling smile. “C’mon,” Dean says, and takes Cas’ hand, pulling him down the stairs, past the patio and all the way to the beach.

The sand is uneven, causing them to stumble in their dressy leather shoes, but it doesn’t seem to matter. Nothing seems to matter, except for the way Cas’ eyes glint in the unearthly light of an almost-full moon, the way he leans into Dean’s shoulder every time he loses his footing, the way their fingers fit together like they were always meant to be this way.

Just as Dean begins to lose his resolve to walk any further, they round a small rock formation. Behind it is a sandy nook, sheltered from view by the rocks and far enough from the water that any other late-night beachgoers would hardly think to venture there.  Satisfied, Dean pulls Cas along until they collapse, laughing, onto the sand.

They come to rest side by side, and Dean reaches out, running the backs of his fingers along Cas' lightly stubbled cheek. Cas brings Dean’s hand to his lips, pressing a kiss to the center of his palm, murmuring endearments against the callused skin of his fingers.

“Kiss me, Cas,” Dean whispers, and leans closer, catching Cas’ lips with his own. It’s slow and languid, unhurried and sweet. The taste of alcohol still lingers on both their tongues, just enough to enhance the pleasure. Dean climbs up to straddle Cas' lap, pressing down to feel the growing hardness between the other man's legs. 

“You’ll put creases in my good suit if you keep on like this,” Cas murmurs, his lips curving up even as Dean leans down to kiss him again.

“Well, then,” Dean says, placing a constellation of nips and licks against the length of Cas’ throat. “We’d better take it off.”

Cas moans softly into their next kiss, heating and fanning the smoldering spark in Dean’s belly until it turns to open flame.

Hands clumsy, Dean pulls at his suit jacket, dumping it unceremoniously in the sand next to him, then paws at his waistcoat. Cas’ fingers dislodge Dean’s, undoing the buttons with shaking fingers. By the third one down, however, his patience seems to fail him, and he pulls Dean close again, licking at the seam of his lips.

“Taking too long,” Cas pants against Dean’s cheek. “Want you now.”

Dean nods, trailing open-mouthed kisses along the sharp line of Cas’ jaw. “Yeah. Sure, Cas. You’ve got me.” He sits up in Cas’ lap and unbuttons his trousers, palming the prominent bulge in his underwear. “Next time, we’ll lose the clothes and do this in a bed though. Promise?”

“I promise,” Cas says, face alight with the anticipation of things to come.

Dean stills for a moment, looking down at the beautiful man beneath him. It’s hard to believe, now, that he was ever going to choose anyone, anything, other than this.

“Dean,” Cas breathes into the space between them. “Please.”

Beyond words, Dean nods and reaches down to undo the button and fly of Cas’ suit pants. Next, he addresses himself to the line of buttons at the front of Cas’ underwear until his cock springs free, thick, flushed red and weeping at the tip.

“So beautiful,” Dean murmurs. He bends down, taking Cas’ length into his mouth, tongue swirling around the tip as Cas moans and writhes beneath him, hips thrusting up in an eloquent plea for  _ more _ .

Dean obliges, sinking down lower. It’s been some time since he’s done this, chances for intimacy with other men being few and far between even in his chosen career and milieu. He hollows his cheeks and bobs his head, the soft, desperate sounds that spill from Cas’ mouth sending more blood to his own rock-hard length.

Cas taps his shoulder, and Dean pulls off to find him thoroughly ravaged: lips kiss-bitten and swollen, cheeks flushed, hair ruffled, shirt, waistcoat and jacket in disarray. “Not yet,” Cas says, between panting breaths. He holds up his hands, reaching for Dean. “Come up here. Let me return the favor.”

Heartbeat picking up and fire pumping through his veins, Dean obliges, clambering up the length of Cas’ prone body until he’s perched over his chest, pushing down his pants and underwear just far enough to free his erection. Cas pulls him close, plush lips wrapping around Dean’s length, and Dean’s arms nearly buckle from the wet, intoxicating warmth of it.

“Cas,” he breathes, hips rocking gently into the motion of Cas’ jaw around him. Cas opens his eyes, hungry and lust-darkened, and tightens his grip on Dean’s rear, pulling him in closer, encouraging him to keep moving.

All the breath in Dean’s lungs escapes him at once as he feels his tip hit the back of Cas’ throat, feels the way Cas relaxes around him, then  _ swallows _ .

With a desperate shout, Dean finds his release, pouring down and into Cas, the act somehow so much more than merely physical: a promise of more. A promise of a future.

He collapses onto Cas’ chest, hand fisting the lapel of his suit jacket, Cas’ still-hard cock now trapped between them. Cas hisses at the sensation and arches his back, and Dean props himself back up on shaking hands. “I can—” he begins, already starting to move back down Cas’ body, but Cas grips his arm to stop him.

“Dean, I want—” Cas licks his lips, eyes flitting to the side. “I’d like to… bring myself to completion. While you watch.” He looks back at Dean, uncertain. “Perhaps I could…” A warm hand slides underneath Dean’s waistcoat and shirt, running suggestively down his chest and stomach.

Dean’s heart, barely recovered from his recent climax, beats faster again at the mere thought of what Cas is suggesting. “Yeah, Cas. Absolutely.”

He climbs off Cas’ lap on shaky legs and lies down on his back, undoing the buttons of his waistcoat and shirt as he goes, until his chest is laid bare. Cas climbs on top of him, tongue darting out of his mouth to lick his hand before he grasps his hard, weeping length, hips moving into the tunnel of his fist. Dean is mesmerized by the sight of Cas’ cock disappearing and reappearing between his fingers as he moves, his own length trying its hardest to stir as Cas rocks on top of him.

It takes no more than another few strokes before Cas spills, releasing warm and sticky onto the skin of Dean’s chest. Dean’s breath hitches at the sight of Cas’ pleasure-slack face, eyes closed and lips parted around a soft moan. 

Cas sits back on his heels, breathing heavy, pure bliss etched on his features as he smiles down at Dean. 

His smile dims slightly as he considers the mess on Dean’s chest. “How on Earth are we going to clean this up?”

Dean chuckles fondly. “That’s what pocket squares are for, Cas.”

“I always wondered,” Cas says, deadpan, as he reaches for Dean’s suit jacket, bunched up on the sand next to them, and retrieves the square of emerald silk. Dean wipes up the worst of the mess, then discards the soiled fabric somewhere out of sight and pulls Cas down on top of him, chest to chest, Cas’ head tucked under his chin.

“Wanna stay like this,” Dean whispers. “Just for a minute.”

Cas presses a kiss against Dean’s collarbone and wraps an arm around his middle, holding on tight.

*** 

By the time Cas blinks back to awareness, the sun is up, bright rays reaching even into their little beachside hideaway.

He seems to have fallen asleep curled against Dean’s side. But he's also resting on the unforgiving sand, and he’s achy in parts of his body that he’s rarely had occasion to be aware of before. With a disgruntled groan, he sits up, rubbing at the juncture between his neck and shoulder. Next to him, Dean shifts, mumbling incomprehensible nonsense and doing his best to pull Cas back down.

“Dean.” Cas nudges Dean’s side, gently but pointedly, even as he takes stock of his own clothing. His suit is badly rumpled, and covered with sand, but it’s nothing a thorough dry cleaning won’t fix. A good thing, too, as it’s the only suit fit for performing that Cas owns.

“Dean.” He nudges again, closer to a shove this time, and Dean rolls away from him, cursing. “We need to go, Dean. The sun is up. People will be wondering where we got to. If Adler finds out we never made it back to our room last night, he’ll throw us both out of the band.”

Dean sits up, wide-eyed. “Shit.” He looks down at himself, obviously trying to grasp where he is, and why. “Where’s my suit jacket?”

“Over here.” Cas picks up the discarded item, even more rumpled and sand-covered than his own suit. He squints at it, considering. “Probably salvageable? The pocket square is a total loss though.” He jerks his chin at the item in question, bunched up in the sand next to where Dean is now sitting and rubbing at his eyes with the heel of his hand.

Dean grins down at the ruined piece of cloth. “Worth it.” He looks up, and his face softens. “Come here.”

Cas is helpless to resist, so he leans forward and lets Dean tug him closer by the back of his neck. The kiss is chaste, tender, but all the more toe-curling for it.

“Alright,” Dean says, pulling away, his resolve to face the day evidently strengthened. “We’d better get moving, I guess.”

With a curse and a creaking of joints, Dean levers himself off the sand, and they make their slow, meandering way back along the coastal highway to the hotel. Once they come in view of the building, Dean decides it’s best to split up.

“That way,” he says, “if Adler’s on the prowl, he won’t catch both of us. If I run into Adler, I’ll convince him I was out for a morning stroll.”

Cas frowns. “In your suit from last night?”

Dean waves the objection away. “So maybe my other suits are at the cleaner’s. We’ve gotta work with what we’ve got, Cas. Anyway, like I was saying, a morning stroll, and I spent all night in my room with you, like a good little boy. You’ll back up my story, of course.”

“And if  _ I _ run into him?”

“Easy. Same thing in reverse.”

Cas bumps his shoulder into Dean’s as they make their way up the path that leads from the highway to the hotel. “This story has more holes than a Swiss cheese.”

“Maybe,” Dean says, conceding the point with an easy smile. “But even if we do get into trouble, I’ve got no regrets.” He returns Cas’ shoulder bump, something almost shy in his expression. “Do you?”

Cas grins, happy and carefree. “None.”

They split up near the top of the path, Cas walking around the building to one of the back entrances, and Dean heading to the front. Cas spares Dean a last glance as he walks away, enjoying the way the morning sun paints Dean’s skin a particularly pleasant, pale gold color.

He turns to resume his way around the building and, soon enough, reaches the porch steps that lead up to the rear entrance. He finds himself in a corridor near some conference rooms, with a large table set up between two doors. 

A young man sits behind the table, chair tipped back on its hind legs, looking bored as he flips a silver half-dollar in the air and catches it. He straightens when a small group approaches from the far end of the corridor. Cas lowers his head as he draws closer, making himself as unobtrusive as possible; just in case Adler is around.

“Delegates,” the young man says. “Welcome to our annual conference of ‘Friends of Italian Opera.’ I gather I’m addressing Mr. Crowley and friends, from the South Side chapter of Chicago?”

Cas’ heart skips a beat, blood freezing in his veins and knees threatening to buckle under him. With a superhuman effort, he forces his feet to keep carrying him further down the corridor, but at the first opportunity, he ducks into an open doorway and peers cautiously at the reception table.

Even at a distance of some twenty feet, there’s no mistaking the bone-white gleam of a pair of spats. 

*** 

In hindsight, perhaps Dean shouldn’t have gone through the front door.

He makes it exactly as far as the chandelier in the center of the foyer before Adler looms in front of him like a bald-pated, avenging angel.

“Where are  _ you _ coming from at this time of morning, Mr. Winchester?” He casts a disdainful glance at the state of Dean’s suit, which, admittedly, has seen better days. “And in the same clothes you performed in last night?”

Dean gets as far as “Just out for a morning—” before Adler’s hand darts inside his suit jacket, producing his flask.

Adler scoffs. “I should’ve known this wasn’t Novak’s.”

Dean makes a grab for the flask, but Adler dances out of his way, surprisingly graceful for a man his age and size. “Look,” Dean says, pleading. “That flask’s empty, you can check. I just keep it around because it used to belong to—”

Adler’s eyes narrow. “If it’s empty, it’s because you’ve been drinking. Again.  _ And  _ you were out past curfew. This is the last straw, Winchester. I—”

“You’ll return that man’s property if you know what’s good for you.” The voice is deep, gruff and unfamiliar. Dean pivots on his heel to face the newcomer, and vaguely recognizes the man in the cap who caught his eye on the porch the previous day, right after his and Charlie’s run-in with Spats.

Adler puffs up like an offended rooster. “I’ll thank you to stay out of my business, Mr.—”

“ _ Agent _ Benny Lafitte.” The man reaches into the inside pocket of his fishbone coat and produces a badge. “Federal Bureau of Investigation.”

Adler blanches, but doesn’t yield just yet. “Whoever you are, I don’t see what concern it is of yours how I conduct—”

“Well, let’s see here.” Lafitte screws up his eyes in mock thoughtfulness. “I seem to recall that someone fitting your description exactly is wanted for accounting fraud in three different states.” He cocks his head. “Should we take a walk down to the police station together, see if we can’t connect you to one of those cases? Or would you prefer to return this man’s property now?”

Face stiff with silent rage, Adler surrenders Dean’s flask. Without another word, he stalks off in the direction of the elevators.

Dean turns to face Lafitte, grinning. “Fuck. How on earth did you know that?”

Lafitte returns his grin, with interest. “Honestly? I didn’t. Lucky guess. Seen a lotta crooked accountants in my day, and he’s got the exact look about him.”

“Well. Thanks for coming to my rescue.” Dean holds out his hand to shake.

Lafitte takes it. He’s got a firm, solid grip. “You’re welcome, brother, but I didn’t help just outta the goodness of my heart. I’ve got a proposition for you.”

Dean lets out a heavy breath. “People keep saying that to me lately.”

“It ain’t that kind of proposition,” Lafitte says, smirking. “C’mon. Let’s head for the café. I’ll buy you a cup of Joe and tell you what it’s all about.”

The café opens right off the lobby, and it’s a matter of minutes to get settled at one of the small tables, two steaming cups in front of them. “I’ll get right to it,” Lafitte says, scooping three spoonfuls of sugar into the delicate little china cup. “You know Spats Crowley?”

Taking a sip of his own, sugarless coffee, Dean shrugs. “I know  _ of _ him. Kinda hard not to, growing up in the South Side. Haven’t got any dirt on him though, if that’s what you’re after.”

“Nah.” Lafitte stirs his coffee, penetrating eyes studying Dean across the table. “Spats is one of the cases I work, back home, at the Chicago field office. My bosses think I’m tiltin’ at windmills, but I always thought, if I could get him, it’d be when he’s off his guard. You know, someplace that ain’t his home turf. When I heard he was headin’ down here for a mob meetin’ disguised as a conference of opera lovers… well, I figured this was my chance.”

“Where do I come in?”

Lafitte doesn’t answer for a minute, eyes fixed on the view of the beach just outside the tall French windows. “Here’s the thing. I need solid evidence against Spats, and I can’t get it myself. He knows my face. Ain’t no way I’ll be able to sneak into one of their meetin’s without bein’ noticed.”

Dean swallows hard. “You want  _ me _ to help you get the evidence.”

Lafitte nods. “Bureau wouldn’t send any backup down here with me, and I can’t call in the local police without solid proof that somethin’ illegal’s goin’ down.”

“Why me?” Dean asks. “Can’t be just because I’ve seen the guy around a time or two.”

“It ain’t,” Lafitte admits, taking another sip of his coffee. “I had my eye on you even before I knew about that part.”

Dean fishmouths once, twice.  _ Not everything is a flirtation, Winchester, _ he reminds himself forcefully.  _ Besides, you’re off the market now. _

A pleasant, buoyant warmth fills his chest at that thought, and he smiles as he says, “So why?”

“Well,” Lafitte says, leaning forward. “Have you ever heard of a dictograph?”

Dean frowns, thinking. “Sounds familiar. Something to do with covert police work?”

“That’s right. It’s a listening device. Been used to get evidence in a number of big cases, like the McNamara bombing. The transmitter’s small, round, about the size of your ear.” Lafitte tugs at his own earlobe to demonstrate. “It’s attached by wire to a receiver that records sound.”

“Alright,” Dean says slowly. “I’m still not sure how I come into it.”

“Well,” Lafitte says, “it’s small enough to be easy to hide in an office, or someplace else with lots of nooks and clutter. A lot harder to conceal a wire runnin’ across the floor of a conference room.” He lowers his voice, conspiratorial. “You know what makes it real easy though? Hiding the thing in a microphone setup.”

Dean sits up straighter, understanding starting to dawn. “You want me to perform at the conference so I can plant the transmitter.”

Benny nods, grinning. “At the luncheon today, right before the food’s served. Got word from an informant that somethin’s goin’ down around then, somethin’ that involves Spats. Already flashed my badge at the hotel manager, asked him to send word that the hotel’s bringin’ in a singer for a special performance. To show their appreciation for the conference’s business.”

Dean leans back, crossing his arms across his chest. “What made you think I’d even agree to this?”

“Easy,” Lafitte says, mirroring Dean’s posture. “I haven’t told you the best part. There’s a reward for anyone who quote-unquote ‘assists materially’ in the arrest and conviction of Spats Crowley.”

Dean’s heart beats a frantic rhythm against his ribs. “How much?”

Lafitte’s grin widens with the knowledge that he’s won the battle. “Five thousand dollars.”

Dean almost falls off his chair. Five grand. That’d be enough to buy a house. To start a business. Certainly enough to keep him and Cas comfortable together for a good long time.

He holds out his hand to shake. “I’m in.”

*** 

It takes Cas a good twenty minutes to regain sufficient equilibrium to move from his hiding place. Slinking along walls and through dark corners, looking over his shoulder all the while, he makes his slow way to the elevator. Even with the call button already pressed, he thinks better of it and creeps up the stairs instead.

When he reaches the third floor and turns the corner from the landing, he crashes straight into someone walking the other way. After a brief moment of panic, he steps back and recognizes Charlie.

“Hiya, Cas,” she says, cheerfully. “Have a good time last night?” Her smile fades as she takes in Cas’ expression. “Damn, you look like you’ve seen a ghost.”

Cas exhales, willing his blood pressure to return to a reasonable level. “Close enough.”

“Well, I was heading down to the beach to meet up with Dorothy, but I can’t leave you like this,” Charlie says. She grabs Cas’ rumpled sleeve and drags him down the corridor, straight to her room. “What you need is a pick-me-up.”

“No,” Cas protests feebly. “I need to find Gabe. We need to—”

“Not another word,” Charlie says sternly, unlocking her door and pulling Cas inside. She steers him to the foot of one of the beds and produces a pink hot water bottle from the top drawer of a dresser. “This’ll do the trick.” In response to Cas’ presumably confused look, she adds, “It’s not water, if that’s what you’re thinking. The bottle’s just a little insurance, in case Adler decides to go snooping around our rooms.”

She pulls out the plug and offers the rubber bottle to Cas, who accepts it gratefully and takes a deep gulp. The taste is awful, but the burn is somewhat steadying.

“Well, then,” Charlie says, hitching up the legs of her high-waisted trousers and sitting cross-legged on the foot of the other bed. “Talk to me, Cas. Is this about Dean?”

Cas takes another drink, looking down at his scuffed, sand-covered shoes and wondering how much to say. Charlie, however, seems to take his silence as confirmation.

“Oh, Cas,” she breathes. “I’m so sorry if Gabe and I took things too far. We were just aiming to give the two of you a little push, but we never wanted to cause you any trouble or heartbreak, I swear.”

Cas meets her eyes, even smiles a little at the sincere regret he finds there. “It’s not about Dean. But now that you mention, it… God, what do I tell him?” He restores the bottle’s plug and sets it down, covering his face with both hands as realization sets in. “I can’t stay, not now that—”

He breaks off, ignoring the stricken expression on Charlie’s face. “Thank you for your hospitality, Charlie, but I really do need to find my brother. I’ll—”

_ See you later _ , he means to say. But that promise isn’t one he’ll be able to keep, so he simply says, as he turns to go, “Thank you for everything, Charlie.”

He doesn’t wait for a response. The corridor is thankfully empty when he steps into it, and Gabe’s room is only two down from Charlie’s.

Cas knocks, but the only answer he receives is a grunt. He knocks harder. “Gabe! Gabe, I need to talk to you! Now!”

More grunting, then the squeak of bedsprings and a slow, shuffling walk, coming closer. The door opens, and Gabe squints at him, dressed in nothing more than a pair of white cotton underpants, hair in complete disarray, pillow creases on his cheek.

“I swear, this better be important, Cassie. That Josie Knight, I tell ya. She’s a firecracker. Hard to keep up with.”

That news diverts Cas momentarily from his mission. “You were with Josie Knight?”

Gabe’s previous, woebegone expression is wiped off his face and replaced with a smirk. “Apparently, she was jilted by one D. Winchester. Wanted a warm body to cheer her up, and yours truly provided.” He cocks his head, grinning. “You wouldn’t have anything to do with said jilting, would you?”

Cas blushes reflexively, then remembers with a sinking feeling why he came to see Gabe in the first place. “That’s neither here nor there, Gabe. Let me in.”

He pushes past none too gently, looking around the room. “Where’s Garth?”

“Down by the beach, I imagine.” Gabe pulls a disgusted grimace. “He’s a  _ morning pers _ —”

“Spats is here,” Cas interrupts.

Gabe’s slack-jawed gaping would be highly entertaining, if they weren’t one misstep away from being on the wrong end of a Chicago typewriter. “I’m sorry,” Gabe says slowly, putting one finger in his ear and wiggling it. “I must’ve misheard. It sounded like you said  _ Spats _ was here.”

Cas barely suppresses the urge to shake his brother. “We  _ really _ don’t have time for this. We have to get out of here. Now.”

Gabe slumps heavily onto the foot of his bed, rubbing at his stubbled cheek. “Yeah. Yeah, you’re right. I’ve got no plans to retire my sax and play the harp with Toothpick Marv.” He looks up, expression shrewd. “What about Dean?”

Cas clenches his jaw, shuttering his expression as far as he’s able. “What about him?”

“Don’t give me that. I know you, baby bro.” Gabe keeps staring, eyes narrowed. “You’re utterly infatuated with the guy, and you know it.”

“So what if I am?” Cas throws up his hands in a helpless gesture of frustration. “We obviously can’t stay here. We can’t go back to Chicago. We may as well take the next boat to South America and hole up there for the rest of our lives. Is that what I’m going to offer him?”

Gabe winces. “Point, unfortunately, taken.” He gets up and puts a steadying hand on Cas’ shoulder. “C’mon, Cassie. Let’s pack.”

It takes no more than a few minutes to get Gabe more or less presentable and gather up his meager possessions. Suitcase and instrument case packed, they poke their heads into the corridor and, finding no one there, sneak back to Cas and Dean’s room. 

There’s no one inside, which is equal parts disappointment and relief. It would be wonderful to see Dean one more time, but Cas is not entirely certain he could find the words to say goodbye; not when faced with Dean’s gold-flecked emerald eyes, the freckles dotting his nose, the sheer, overwhelming presence of him.

But say goodbye he must, so he sits down at the small desk in the corner, uncapping the hotel-provided pen and dashing off a note on paper with the Coronado’s letterhead.

_ Dear Dean, _

_ I am so sorry, but you will not see me again. Please know that I will always appreciate our time together. _

After a moment’s thought he adds,

_ You’re better off with someone else. This would never have worked. _

He considers a “yours” or “with love,” but thinks better of it and simply signs his name at the bottom. If the note appears curt or callous, so much the better. It will help Dean move on.

Hands only trembling a little, he folds the paper in two, taking extra care to line up the edges, then places it on Dean’s pillow. He feels Gabe’s eyes as a prickle on the back of his neck, but doesn’t acknowledge him.

He has even fewer possessions than Gabe does, so he merely changes into his traveling suit, stuffs his performance outfit and overnight bag into his battered suitcase, and grabs his instrument case in his other hand. 

Already halfway to the door, he feels Gabe’s hand on his shoulder. “Hold your horses, Cassie. We’re not going out that way.”

Cas frowns, confused. “We’re not?”

“No way. What if we run into Spats and his goons in the elevator or in the lobby?”

“I hadn’t considered that,” Cas admits, reluctantly.

“So we climb out the window. The roof is flat just there, and there’s a bit of scaffolding along the near side of the building that we can shimmy down to get to the ground floor.”

“How on earth do you know this?”

Gabe shrugs. “I make it my business to know the fastest way out of any room at any given point.”

“I sometimes have serious doubts as to whether we’re actually related,” Cas says, watching his brother pull up the window sash and climb through the gap.

“Me too, baby bro,” Gabe says, jerking his chin impatiently. “Get a move on.”

With a last, despondent look at Dean’s open suitcase on the floor by the armoire, Cas clambers after Gabe. The roof outside the window is indeed flat, and wide enough that their crabwalk along it isn’t entirely terrifying.

Backs pressed to the wall, they edge along, and Cas makes it a point not to look into any of the rooms they pass along the way. The less attention they invite, the better. Thankfully, the scaffolding is right around the corner, a somewhat rickety-looking wooden structure connected by means of a series of metal pipes.  When Gabe reaches the edge of the roof, he sits down on the tiles to lower himself onto the top level of the scaffolding. The painter looks up, frowning at him.

“Now see here—” the man starts, but Gabe interrupts even as he hops off the roof.

“Nothing to worry about, my man,” he says jovially. “We are  _ definitely  _ supposed to be here. Special agents in the crown’s service.”

_ What crown? _ Cas mouths, mostly to distract himself as he shimmies to the edge of the roof on his backside and drops down onto the rickety structure.

Gabe shuffles along the wooden slats, edging past the workman, and Cas follows with an apologetic grimace, somewhat off-balance with the heavy case of his bass fiddle in one hand. Gabe unceremoniously dumps his own luggage into some bushes underneath an open window on the ground floor. Both hands now free, he shimmies down the metal pipe that leads to the lower level of the scaffolding. With a wince, Cas hands down his suitcase and instrument, watching as Gabe drops them into the bushes as well.

Cas follows his brother down the pipe to the lower level, noting that the window seems to belong to some manner of conference room that is, thankfully, unoccupied. He turns away, intent on climbing off the scaffolding’s lower level and onto the ground so they can retrieve their luggage. 

That’s when he notices Gabe hasn’t moved. He’s frozen, staring at the walkway that leads to the hotel’s main entrance. Cas follows the direction of his gaze.

Spats Crowley is strolling up the walkway, not fifty feet away, flanked by his usual escort of goons. He doesn’t seem to have spotted them yet, but it’s only a matter of time. Gabe, always a quick thinker if not usually a wise one, grabs Cas by the arm and pushes him, none too gently, through the open window into the conference room.

It’s still empty, nothing but a small serving table, a microphone, and some two dozen unoccupied chairs lined up along three long tables. The tables have been pushed together in a horseshoe shape, and they’re covered in floor-length cloths.

Cas and Gabe start walking towards the double doors that lead out of the room, but they never make it there. The sound of footsteps — not just one set, but dozens — echoes along the corridor beyond the doors, approaching rapidly.

“Quickly,” Gabe hisses, tugging at Cas’ sleeve. “Under the table!”

They lift up the edge of the nearest tablecloth and shuffle under it just as the doors open and what sounds like a sizable crowd walks in, pulling out chairs to sit down.

Cas and Gabe instinctively tuck their limbs in, making themselves as small as possible, and Cas sends up a fervent prayer that, by some miracle, no one is going to sit in the chairs nearest them.

When the chair by his elbow is pulled out, Cas knows there is no God. 

The man who is even now making himself comfortable, shoes tucked under the tablecloth less than two feet away from Cas, is wearing white spats.

**Notes for the Chapter:**

> The dictograph [really was used as a covert listening device in criminal investigations](https://archive.org/details/worldswork24gard/page/37/mode/2up), including the McNamara bombing case in 1911.
> 
> Next time: Spats faces a reckoning. Cas has some decisions to make about his future. Dean is through with love - or is he?


	5. Chapter 5

**Notes for the Chapter:**

> ... and that's it! Thank you all so much for coming on this journey with me! I hope you enjoyed yourselves. <3
> 
> The song in this chapter, "I'm Through With Love", is performed by Marilyn Monroe in the movie. Here's [a great recording](https://www.youtube.com/watch?v=tPZGM165PIg).

It's just before eleven when Lafitte is finally satisfied that Dean has a solid grasp on what he's supposed to do.  (And what he _isn't_ supposed to do: mainly, take stupid risks and get himself into trouble. Dean figures it's lucky Lafitte doesn't know him very well, or he might never have offered him the job in the first place.)

Dean's performance in front of the so-called Friends of Italian Opera is supposed to take place at eleven thirty, so there's barely enough time to make himself presentable. 

As he hurries back to his room, his suit jacket hangs lopsidedly off his shoulders, a heavy object weighing down one of the pockets. It's a circular, roughly fist-sized apparatus, with a wire that attaches to it on one side. The wire’s other end is meant to connect to the receiver that Lafitte’s going to set up in a supply closet next to the conference room.

The obvious question now, Dean considers, is what his performance should even look like. The most appropriate tune for an ostensible gathering of opera lovers would be an aria, but those aren’t exactly part of his standard repertoire, and there’s no time to rehearse. 

After a minute's deliberation, he settles on “You’d Be Surprised.” He knows the lyrics, and the accompaniment is easy to adapt for his ukulele. Not to mention, after last night, he has extremely fond memories of that song. He could use those memories to steady him while he’s putting on a show for the leading lights of the Midwest mob.

When Dean walks through the door of his room, Cas isn’t in evidence, which is just as well. Sure, Dean would’ve liked to see him, maybe get a kiss for good luck before he goes back downstairs, but all things considered, there’s too much explaining to do in too little time. If he’s entirely honest, he also doesn’t want to get Cas’ hopes up about the reward, just in case it doesn’t pan out.

Dean pulls off his suit, leaving it at the foot of his bed to remind himself that he needs to get it cleaned before tonight’s performance. As he turns away to head to the bathroom, something catches his eye — a small, neatly folded square of paper, centered perfectly on his pillow. Dean smiles down at it. Probably a note from Cas, to let Dean know where he’s gone.

He unfolds the note, the smile sliding off his face as he reads. And reads again. And once more.

For the first time, Dean takes a thorough look around the room, and notices the emptiness all around him. Cas’ instrument case is no longer on the floor next to the window. His suitcase isn’t on the luggage rack by the armoire. In fact, there’s no evidence at all that Cas was ever here.

_ You’re better off with someone else. This would never have worked. _

Dean crumples up the note in his fist and flings it at the frame of Cas’ bed, the closest thing he has to a stand-in. It’s not even remotely satisfying.

The clock on the desk ticks away the minutes until performance time. Only twenty of them left now. Maybe Dean should just blow the whole thing off; let Lafitte find some other stooge to help him. What’s the use of a reward if he doesn’t have Cas to share it with?

Dean rubs at his temples, willing his brain to work around the white noise of hurt and confusion. No, he’s  _ got  _ to go through with this. There’s still his ma to think of. He went on this damned trip because he wanted to take care of her. Now he’s got a real chance to make some cash, and he’s going to let it pass him by over a broken heart?

Dean blinks hard, once, twice. He squares his shoulders and pushes everything down. He’ll deal with it later. For now, he’s got a notorious gangster to entrap.

It takes him no more than ten minutes to shave and change into his day suit, a plain but presentable brown wool number, classed up with a purple tie and matching pocket square. He grabs his ukulele and heads down to the conference room where Lafitte told him to go. There’s a youngish hoodlum guarding the door, looking bored and tossing a silver half-dollar up in the air.

Dean walks right up and gives the guy a big, cheery grin. The less threatening he can make himself look, the better. “Morning,” he says, all easy nonchalance. “I’m the singer? Was told to come down here for some pre-lunch entertainment.”

The hoodlum, a weaselly guy whose floppy-brimmed hat is pulled too far down his face and whose pinstriped suit probably costs more than Dean makes in a year, gives him the once-over. “Heard someone was comin’,” he concedes. “Lemme see that.”

He reaches out a grabby hand for Dean’s instrument case, presumably to check for concealed weapons, and Dean reluctantly hands it over. “Alright, but watch my baby. She’s delicate.”

The goon snorts as he unclasps the case and lifts up the ukulele, none too gently at all, to paw at the lining. “Checks out.” He beckons Dean closer. “Arms out, and spread your legs.”

The line,  _ Geez, buy a girl dinner first _ is right on the tip of Dean’s tongue, but he swallows it. It doesn’t do to antagonize the mob. So he lets himself be patted down from head to toe.

“What the hell’s this?” the guy asks, pulling the transmitter and wire out of the inside pocket of Dean’s suit jacket.

“Part of the microphone setup,” Dean lies, hoping his face doesn’t give him away. This is the only really tricky part. If the door guard doesn’t swallow the story, there’s no way he’ll get inside. “Helps scatter the input, you know, to keep from overloading the grid.”

All of which is complete gibberish, but, against the odds, this guy seems to be the sort who’s inherently impressed by jargon. “That’s real interesting,” he says, looking thoughtful. “The things they can do nowadays, huh?”

Dean nods fervently, sweat pearling on his neck. “It’s something else,” he agrees, and tries not to let his relief show when the guy motions for him to proceed. He walks in at Dean’s back and closes the door after himself, as Lafitte predicted he would once all the expected guests were inside the room. If everything’s going according to plan, Lafitte’s already waiting somewhere nearby until he’s sure the coast is clear, dressed in a hotel uniform and with the receiver concealed under a cloche serving dish.

Dean spots the microphone setup at the far end of the room, past a row of three tables arranged in a horseshoe shape. Behind each table, the conference “delegates” are seated, murmuring quietly to each other. A prickle of unease runs down Dean’s spine, and he makes sure not to look at anyone too closely. 

Instead, he walks over to the microphone. A bunch of electric cables are connected to it, running along the floor and all the way to the supply closet next door, where they’re presumably plugged into an outlet. The closet door has a sign marked “Staff Only” to discourage interlopers, and, according to Lafitte, there’s a second door that connects to the corridor outside. Dean has a feeling the guy pulled some strings to have the luncheon held in a room with ideal conditions for his snooping operation.

He sets down his ukulele and starts fiddling with the cables attached to the microphone, doing his best to make the motions look routine and practiced. Next, he pulls the transmitter out of his pocket, connecting it to its wire and mixing it in with the other cables already running along the floor.

The transmitter, Lafitte told him, should be placed as unobtrusively as possible, just in case anyone tries to investigate the setup. So Dean walks along the length of cables until he gets to a spot where it runs close to a small side table. He places the transmitter right behind one of the table’s legs, making sure to put his back to the room so no one can watch him too closely.

That task accomplished, he runs the wire the rest of the way to the closet door and steps through it. The closet is cluttered with various odds and ends — cleaning supplies, mostly, but also an odd assortment of mismatched chairs and serving trays.

Dean double-checks that the access door to the corridor is unlocked, then leaves the wire on the floor, ready to be plugged into the receiver when Lafitte gets here.

Satisfied that he’s done his part, Dean backs out of the closet and closes the door behind him, then retrieves his ukulele from its case. He takes his place behind the microphone, flicks the switch to turn it on and clears his throat to get the audience’s attention.

“Morning, gents,” he’s about to say, but he stops short, mouth open and eyes caught on the end of the nearest table.

Something’s moving underneath the tablecloth. For the briefest flash of a moment, something darts out from under — a hand? But it’s gone again so quickly, he can’t be sure. He chances a glance around the room. No one else seems to have noticed anything amiss.

Dean may not know a lot about the mob, but he knows it’s bad news to have someone hiding under a table during a big meeting. There’s about to be trouble, and Dean’s going to be right in the middle of it.

But what choice does he have? If he leaves without giving his performance, he’d only arouse suspicion — not to mention, Lafitte needs everyone in here and looking at Dean while he sets up the apparatus next door — so his best chance is just to get his song done quickly and blow the joint. Once he’s done that, he can let Lafitte know what’s going on.

So Dean clears his throat again, and says, “Morning, gents. This tune is called, ‘You’d Be Surprised.’”

He makes a few final adjustments to the strings of his ukulele, then starts strumming the tune. He plays it a little more slowly than he usually would, not unlike the way the Cuban band did last night.

By force of habit, his voice shapes itself around the words, but there’s a band of iron squeezing at his chest, making it almost impossible to draw the full breaths he needs to keep his voice steady. So much for pushing down the hurt until later.

_ He's not so good in a crowd but when you get him alone _

_ You'd be surprised _

_ He isn't much at a dance but then when he takes you home _

_ You'd be surprised _

A few of the audience members are watching him, but most are too busy whispering to their neighbors along the table. There seem to be a lot of dirty looks being exchanged, mostly between Spats Crowley and the guy at the head of the table, a weather-beaten, sneering individual whom Dean thinks he recognizes as Little Lucifer, head honcho of the North Side mob.

He didn’t think the South Side and North Side crowds were too friendly, and he tries to focus on that bit of oddness, instead of letting himself dwell too much on the words of the song. _Their_ song.

_ He doesn't look like much of a lover _

_ But don't judge a book by its cover _

_ He's got the face of an angel _

_ But there's a devil in his eye _

When Dean finally wraps up, there’s barely a trickle of applause. Figuring he’s done his duty, he goes to stow his instrument and hoof it out of the room so he can go talk to Lafitte.

Then something occurs to him: he might have been imagining things earlier. For all he knows, he’s worried about nothing, and he’s about to send a federal agent on a wild goose chase after mysterious assassins who aren’t there.

Snapping the instrument case shut, he strides past the end of the table — a little closer than necessary, but not so close as to attract real attention. He stops, looks down at his shoes, then crouches, pretending to retie his laces.

He nudges the tablecloth with his elbow. Someone flinches away.

Smiling grimly to himself, Dean rises off the floor, grabs his case and makes for the corridor.

*** 

Something bumps into Gabe’s side, and he flinches away.  _ This is it _ , Cas thinks to himself, a cold sweat prickling on the back of his neck.  _ We’ve been discovered. _

Limbs cramping where they’ve been tucked in at an awkward angle for too long, Cas waits for someone to reach under the tablecloth and pull him out. He tries to resign himself to the prospect of his violent death, as much as possible on such short notice. 

But nothing happens, and the conversations around the table continue as before. Gabe grins, obviously relieved. Cas tries to feel the same, but he’s already feeling too many things, and there doesn’t seem to be room for any more.

There’s the fear of being discovered, sure, and the physical discomfort of being crouched under the table. But above all, there’s a deep, searing heartache that began as soon as he heard Dean’s voice, singing  _ that _ song, _ their  _ song. Hearing the way Dean’s voice was just a little less booming, just a little more unsure, the knowledge came to him, irrefutable:  _ I love him. I should never have left him. _

It’s a hell of a thing to realize just a little too late, and in a life-threatening situation.

Cas shifts minutely, suppressing a curse at the cramp that’s developing in his right calf. They’ve been under the table for a good fifteen or twenty minutes now.

Suddenly, there’s a shuffling of feet, a scraping of chairs, and then a loud, sneering, unfamiliar voice fills the room.

“Fellow opera lovers. It’s been ten years since I elected myself president of this organization. And if I say so myself, I made the right choice.” Subdued applause from a few corners, but none from Spats’ faction, as far as Cas can tell. “Let’s look at our record. We have fought off the crackpots who want to repeal Prohibition and destroy the American home. We have stamped out the fly-by-night operators who endangered public health by brewing gin in their own bathtubs. We are helping the automobile industry by buying trucks, the glass industry by buying bottles, and the steel industry — well, you know, all those corkscrews.” The speaker lowers his voice, conspiratorial. “In the last fiscal year, our income was a hundred and twelve million dollars before taxes. Only, we ain’t paying taxes.” A ragged cheer, and even in the gloom underneath the tablecloth, Cas can see Gabe roll his eyes.

“Of course,” the speaker continues, “we’ve had our little misunderstandings. Let us now rise and observe a moment of silence, in memory of six of our members from Chicago’s North Side chapter who are unable to be with us tonight.” Another shuffling of chairs, louder this time, and Cas makes himself impossibly smaller against the corner of the table. 

But Spats and his companions do not rise.

The speaker seems to have noticed this as well, because he says now, a sharpened edge of menace to his voice, “You too, Spats. Up!”

With a slow reluctance that’s obvious even from Cas’ vantage point, Spats and his companions’ feet disappear from underneath the tablecloth.

“Now,” comes the speaker’s voice. “A man who knows his history might be aware that some of those cats and I, we were real close growing up. Matter of fact, Toothpick and I were choirboys together.”

Cas watches Spats’ knee nudge the tablecloth as he adjusts his stance, betraying either anger or nervousness. “Toothpick was an informant,” Spats says, the rage in his voice barely leashed. “He cost me one of my most valuable operations. He needed rubbing out, and I took care of it.” After a beat, he adds, hissing, “That’s _ real _ leadership, one might say.”

“Oh,” the other speaker says, mocking. “Is _ that _ what one might say?” A breathless hush has fallen over the room. Cas’ heart does its best to escape by way of his throat. “One might also say,” the man says, low, dangerous, “that I  _ told  _ Toothpick to call in that tip, to strike a blow against an uppity South Side operative.” An actual gasp from the crowd. Cas barely suppresses one of his own. “One might say that someone who cost me one of my most valuable  _ operatives  _ is someone who needs, as you so eloquently put it,  _ rubbing out _ .”

Next to Cas, the tablecloth shifts as Spats and his associates turn back and forth, looking for a way out.

There’s the unmistakable sound of a gun being cocked.

_ Bang! _

The double doors hit the wall as they fly open, and Cas flinches so hard, he almost loses his balance. Someone strides into the room. In the corridor outside, at least half a dozen other people seem to be approaching.

“I’d put that down if I were you,” a new voice says, deep, booming and confident, and presumably addressing whoever pulled the gun. The rest of the group is now entering the room.

Cas watches in horrified fascination as Gabe bends down to peek under the edge of the tablecloth.  _ Police _ , Gabe mouths, grinning.

“Now, where was I,” the newcomer says. “Oh, that’s right. Fergus ‘Spats’ Crowley, you’re under arrest for the murder of Toothpick Marv and five of his associates. Got your confession on the record, nice and clear on the dictograph next door.” There is a quick shuffle of feet as Spats and his goons presumably try to make a getaway. “Now, now, none of that. Slap the bracelets on ‘em, boys!”

A commotion, and then, from the original speaker, angrily, “I don’t take kindly to my meetings being interrupted. We’re a perfectly respectable organization of opera lovers, gathered here legally to celebrate the beautiful art together.”

“Tell it to the other one, Lucifer,” the policeman retorts. “I’ll be gettin’ back to that bit about not payin’ taxes some day soon, friend.”

Tense silence, then Spats pipes up. “You might think you’ve won, Lafitte, but recordings have a way of disappearing when you know the right people.”

“As do witnesses, ain’t that right?” the man called Lafitte says, voice heading for the exit. “Word is two men were seen runnin’ from the scene of the Toothpick Marv killin’, but we ain’t ever found them.”

With staggering clarity, Cas realizes what has to be done. Unfolding his painfully aching limbs, he ducks out from under the table, pulling a reluctant Gabe along with him.

Ignoring the gasps and shouts at their sudden appearance, he heads for the door, still dragging Gabe by his sleeve. Spats and his associates are just outside, in the custody of half a dozen uniforms and one burly, broad-shouldered man in a fishbone coat.

“Excuse me,” Cas says, “but you’ve found us  _ now _ .”

Spats spins around, as fast as his shackled hands will allow, and his eyes widen in an almost comical expression of shock. “You!”

Next to Cas, Gabe grins, wide and cocky. “Surprise!”

*** 

When Dean knocks on the door of the supply closet, using the combination they agreed to ( _ long-short-short-long-short _ ), Lafitte answers almost immediately. He’s dressed in the uniform of a hotel waiter and the receiver sits on a serving cart behind him, a red light blinking to show the machine is recording. Low, tinny voices sound from a set of headphones plugged into its side.

“I think there’s gonna be trouble,” Dean whispers, wasting no time as he steps inside and closes the door behind him. “There’s at least one guy hidden under the table, right by where Spats is sitting. I saw him move. Felt him flinch, too, when I managed to nudge him with my elbow.”

Lafitte’s eyes narrow, stern and disapproving. “Took it too far, Dean. Your brief was to get in, place the transmitter, sing, get out. No risky business.”

Dean shrugs, trying not to show that he’s still feeling jittery. He’s got his pride, after all. “It was alright. Nothing happened.” Lafitte opens his mouth, looking like he wants to argue some more, but Dean cuts him off. “I wanted to make sure of what I saw, and I did. Point is, I think you’d better call for some reinforcements.”

Lafitte nods grimly. “Reckon I better.” He grips Dean’s arm, fixing him with a penetrating stare. “Listen. You call the number on this card.” He passes Dean a small cardstock square. “It’s the local police superintendent. He knows me, and he’ll send a contingent if you mention my name. Half a dozen men ought to do it.” Dean nods and turns to go, but Lafitte holds him back. “Once you make the call, you go to your room and you stay there until I get in touch, understood?”

“Understood,” Dean says, already despondent at the thought of being stuck in his room, with nothing for company but the gaping hole Cas left behind.

Lafitte nods. “Good. Soon as the dust settles, we’ll talk about that reward.” He claps Dean on the shoulder, grinning. “You did good, brother.”

Dean nods his thanks and, after a careful look up and down the corridor, steps outside and heads for the phones in back of the lobby.

The call takes no more than a few minutes. Mentions of Lafitte’s name seem to grease the wheels of justice nicely, both with the superintendent’s secretary and with the man himself, who promises to send a detachment of six officers right away.

His mission accomplished, Dean heads upstairs, closes the curtains and lies down flat on his bed, suit and all, hoping for sleep.

But sleep doesn’t come, and he’s treated instead to a picture show of memories from the previous night. Cas’ eyes, gleaming azure under the fairy lights. Cas’ lips, parted in pleasure on the beach. Cas’ solid warmth, curled up and breathing deep against Dean’s chest.

Dean wants nothing more than to drown his sorrows, but he doesn’t have any bourbon left, the last few sips used up for courage before his guest stint with the Friends of Italian Opera.

Maybe after he makes it through tonight’s performance, he’ll head back to the roadhouse, blow his paycheck on a bottle of hooch, and curl up somewhere quiet to lick his wounds.

About an hour later, the phone on his bedside table rings. When Dean picks up, the tinny voice of the hotel operator sounds from the other end of the line. “Line Adam 47, calling for D. Winchester. May I connect your call?”

“Sure, what the hell,” Dean mumbles. It’s probably Lafitte.

As predicted, after a moment, the agent’s deep, booming voice emerges from the earpiece. “Dean. Good to know you’ve stuck to your room, brother. Just calling to tell you we’ve got Spats, and you’ve got that reward coming your way. Probably have to split it with two witnesses who came forward just today, but—”

“That’s great,” Dean says tonelessly. “Singer Agency in Chicago’s got my contact details.”

Without further ado, he hangs up the phone and goes back to staring at the ceiling.

He must’ve nodded off, because some time later, he startles awake to the sound of a knock at his door. It’s insistent and excitable in a way only one person could possibly be. 

“Go away, Charlie,” Dean growls, pitching his voice just loud enough to be heard in the corridor outside. A reluctant glance at the window tells him the sun is already getting low in the sky.

Unfortunately, Charlie never was very good at following instructions, so she strides right in. Her face is aglow, and she’s bouncing on her heels. “Did you  _ hear _ ? About  _ Adler _ ? He’s gone!” She vibrates over to Dean’s bed, flopping down at the foot of it. “Just packed his bags and left, sometime this morning. Didn’t so much as leave a note, but there’s rumors of scandal all over the band. And Dorothy saw a bunch of coppers leading some goons out in handcuffs. None of them were Adler, but it’s gotta be related somehow, right?”

Dean doesn’t answer.

For the first time, Charlie seems to take in the set of Dean’s features, and the happy, glowy smile fades from her face. “What’s going on? You look awful.”

Dean swallows, knowing from painful experience that he won’t get away with refusing to talk to her. So he settles on the shortest possible version of events. “Adler ain’t the only one who’s gone.” He gestures at the room around him, hoping it’s enough to get his point across. 

It seems to be, because Charlie’s face falls, mouth opening in a quiet  _ oh _ . “I’m so sorry,” she says, quietly. “C’mere.”

Dean sits up and lets himself be held, just for a minute. Charlie’s arms aren’t as thick and solid as Cas’, but the warmth of her is comforting all the same.

“Really thought we had something,” he says into the thin, soft fabric of her blouse. “Shows what  _ I _ know.” He clenches his jaw until it’s painful, clutching at Charlie’s back. “Already broke it off with Josie and everything. I even found a way to make some money, get Cas and me set up together.” He pulls back, blinking hard against the prickling in his eyes. “Guess the son of Charles Novak didn’t wanna throw in with some washed-up crooner who never even finished school. Can’t say I blame him.”

Charlie pulls back, surprised. “Cas is Charles Novak’s son?”

Dean nods. “Hasn’t been doing him much good. All the Novak assets are frozen. He’s just as dirt poor as the two of us.”

Charlie dismisses that fact with a wave of her hand. “Those assets are only frozen until someone with real influence complains about it, mark my words. Anyway. Point is, you’re not some washed-up crooner, kiddo. You’re a catch. Even Josie Knight knew it.”

Dean scoffs. “She wanted me for my face. That’s all I’ll ever be good for: looking good in pictures or on stage. Ain’t ever gonna find someone who wants the rest of this mess.”

“You listen to me.” Charlie grabs both of Dean’s hands from where they’re resting in his lap. “You _ are _ a catch, Dean Winchester, and don’t you forget it. If it weren’t for your man parts, I’d snap you up myself.”

Dean chuckles wetly at that. “My loss.”

“No kidding,” Charlie grins. “If anyone’s  _ more _ of a catch than you, it’s me. But seriously, pal. This isn’t on you, understood? I ran into Cas earlier, and he looked like death warmed over.”

“Probably realized what a mistake he made, spending the night with me,” Dean says, each word slashing at his throat like razor blades.

Charlie nudges his chin with her fist until he meets her eyes. “I really, really don’t think so. He  _ said  _ it was nothing to do with you. Just kept talking about how he didn’t know what to do, and how he needed to find his brother. Whatever went down, I don’t think he  _ wanted _ to leave you.”

A tentative blossom of hope tries its best to unfurl in Dean’s chest, but he stomps on it. “Doesn’t matter why he left. He’s gone, and I ain’t ever gonna see him again.” He squares his shoulders and wipes at his cheeks, making sure no wetness is left there to give him away. “And anyway, we got a performance to put on. Better get ready.”

Charlie bites her lip, thoughtful. “Suppose we’d better tell Donna we’re short a bass fiddle. And a sax, most likely. If Cas is gone, I doubt Gabe stuck around.”

“We’ll tone it down on the jazz, do some piano numbers instead,” Dean says, with a passable imitation of indifference. “We’ll manage. Always did before.”

From the melancholy look in Charlie’s eye, she understands that he’s not just talking about the band anymore.

*** 

Cas and Gabe spend the rest of the afternoon at the Palm Beach police station, giving their witness statements first to Lafitte, then to a local sergeant.

By the end, Cas barely hears the questions anymore, concerned only with the constant itch under his skin that urges him to return to the hotel, to talk to Dean and see if what was just beginning between them can still be salvaged.

There is talk of a reward, some outrageous sum that Cas and Gabe will apparently need to split with a third party who made an unspecified contribution. Gabe elbows Cas continually, grinning and talking about how “our money troubles are finally at an end, Cassie,” but Cas can muster little more than a distracted smile.

All things considered, he’d rather be living in a hovel with Dean than in a mansion without him. But considering the dismissive tone of Cas’ note, and the dejection that rang through Dean’s performance of their song, it’s entirely possible Dean will want nothing to do with him ever again.

When Cas and Gabe are finally herded into a patrol car and chauffeured back to the hotel, the sun has already gone down. The silvery light of the moon reflects in the ripples of the sea as the car rattles along the promenade. They turn into the hotel’s driveway and make their laborious way up the hill to the entrance, the car's open windows admitting a pleasant breeze that does nothing to disturb Cas’ gloomy thoughts.

He disembarks when the car comes to a stop and waves a vague goodbye at Gabe, who’s babbling something cheerful about “telling Josie the whole thing.”

Limbs heavy, Cas walks up the porch and into the lobby. On his way to the elevator, he passes the staircase that leads down to the clubroom. From below, the sound of a piano tune, with string backing, reaches his ears.

Even as Cas stops to listen for a moment, a man’s voice starts to sing, weighted with melancholy. He would know that voice anywhere.

_ I’m through with love _

_ I’ll never fall again _

_ Said adieu to love _

_ Don’t ever call again _

_ For I must have you or no one _

_ And so I’m through with love _

Of their own volition, Cas’ feet carry him down the stairs until he’s standing by the main entrance to the club, half-hidden behind the red velvet curtain that frames the doorway.

_ I’ve locked my heart _

_ I’ll keep my feelings there _

_ I’ve stocked my heart _

_ With icy, frigid air _

_ And I mean to care for no one _

_ Because I’m through with love _

Dean is farther away from the microphone than usual, leaning back against the piano at center stage. A spotlight is trained on him and on Donna, whose fingers are stroking the keys, slow and mournful. Dean’s expression tightens as the accompanying string instruments swell behind him.

_ Why did you lead me to think you could care? _

_ You didn’t need me, you had your share _

_ Of slaves around you to hound you and swear _

_ With deep emotion, devotion to you _

On the last line, Dean’s voice cracks, and he lowers his head. Cas’ feet are moving again, carrying him to the front of the room, past the crowded dance floor and to the stage.

He mounts the set of three stairs that lead up to the performers’ level. There’s murmuring from the band and the audience, but Cas pays it no mind. He strides up to Dean, who’s still looking at the floor, waiting for his next cue.

Cas touches Dean’s shoulder, and Dean looks up.

His eyes widen, and Cas notes with a pang of regret that they’re a little red-rimmed. Cas wants nothing more than to kiss Dean and reassure him, right here on stage, for all the world to see. But he knows better.

Hoping his eyes speak for him, he puts into them all the regret and devotion he feels, then jerks his head at the curtain that leads backstage. He starts walking and pulls Dean along by his arm, catching Donna’s knowing smirk out of the corner of his eye.

Even as Dean follows him backstage, looking thunderstruck, Donna rises off her piano stool and motions to the lighting technician to shift the spotlight to the strings, conducting them in a mournful, purely instrumental version of the rest of the song.

Grabbing Dean's hand, Cas pulls him through the thick red velvet of the stage-side curtain and finds himself in a dark, deserted corridor, nothing for company but some disused props and a few ropes and pulleys.

Dean lets go of Cas’ hand and steps away, arms crossed over his chest, expression pinched. “What’re you doing here? Thought you were gone.”

Cas meets his eyes and tries not to flinch at the anger and hurt he finds there. “I was  _ going _ to leave. But please believe me when I say that it didn't have anything to do with you.”

Dean scoffs, half-turning away already. Cas claps a hand on his shoulder, pulling him back. To his tremendous relief, Dean lets him.

“Will you let me explain? Please?” Cas pleads.

Dean stares down at his shoes, but gives a short, jerky nod.

“I guess I’d better start with why Gabe and I went on this trip to begin with,” Cas sighs. “We were on the run from Spats Crowley.”

Dean’s head jerks up, surprise replacing anger for a moment. “What?”

Cas nods. “Gabe and I saw him kill someone named Toothpick Marv. We barely got away, and we knew our lives were forfeit if we stayed in Chicago. So we went to Florida instead.” He huffs a mirthless chuckle. “Except we seem to be the punch line of some terrible cosmic joke, because Spats came  _ here. _ To _this_ hotel, of all places. I spotted him right after I left you this morning. Gabe and I were going to go on the run together, but then—”

Dean swallows hard, frowning. “You and Gabe —  _ you’re  _ the two witnesses?”

“What?” Of all the things Cas expected Dean to say in response to his story, this certainly wasn’t one of them. “How do you know about—”

Dean chews at his lip, eyes back on the floor. “A federal agent, Lafitte, asked me to help him set up some recording equipment. He had a tip that something big was going down. Said if it was something he could nab Spats for, I’d have a reward coming to me.” Dean shrugs, eyes darting back toward the stage, where another song has now started up. “He called me after it all went down. Said Spats got arrested and two witnesses came forward who’d be splitting the reward with me.”

“But Dean, that’s wonderful.” Cas’ face stretches with a relieved smile. “The reward is five thousand dollars. We won’t be poor anymore, either of us.”

“Yeah.” Dean clears his throat, folds his arms more tightly across his chest. When he finally meets Cas’ eyes, his gaze is guarded, challenging. “Bet you’re happy. You get to be rich again. Live the life you’re accustomed to. Forget all about that screw-up musician you had a nice night with once.”

“Dean.” Cas steps forward, still smiling, one hand stretched toward Dean. Dean steps back, and Cas’ smile fades. “I’m so, so sorry about the note. I knew I had to leave, and that I might never be able to come back. I was hoping if I was… dismissive of us and our time together, it might make things easier for you.”

“Yeah, well. It didn’t,” Dean says sharply. “I would’ve come with you, you idiot.”

“What?”

“I said,” Dean repeats, rolling his eyes, “if you’d asked me to come with you, I would’ve.”

“Really?” Hope kindles fiercely in Cas’ chest as he steps forward again. This time, Dean doesn’t back away.

“Really,” he mumbles. “Would’ve wanted to find a way to let my ma know, send her back some money when I could, but—”

Cas closes the distance between them and seals their lips together. It’s uncomfortable, with Dean’s crossed arms trapped between them, but Cas is past caring. Dean steps back almost immediately, looking around and gesturing at the deserted corridor.

“What if somebody saw us?” he hisses. “Are you insane?”

Cas shrugs, feeling loose and carefree all of a sudden. “Possibly. I’m also in love with you.”

Dean shakes his head in disbelief, but Cas can’t fail to note the way his lips are twitching. “You absolute maniac.”

Cas cocks his head. “Why? I don’t have a gangster at my heels anymore, and, at least at the moment, neither one of us is poor. I’d say things are looking up.”

Dean’s lips twitch harder. “Are you forgetting about Gabe? He’s got his share of the reward coming to him too.”

“How could I ever forget about my pest of a brother,” Cas says, grimacing. “I doubt he’ll need to claim his share. After you jilted Josie, Gabe took up with her. If I had to guess, I'd say five thousand dollars is going to seem like pocket change to him soon enough.”

“You’re kidding.” Dean is smiling in earnest now. Cas basks in that smile and what it might mean.

“I’m completely serious,” Cas says, locking eyes with Dean. “And I’m serious about the other thing too. I love you.”

It’s a beautiful thing, watching as the tension melts from Dean’s shoulders, leaving behind nothing but a shy, hopeful grin. “Yeah, Cas. Me too.” He winces. “I meant to say, I love you too. Words aren’t my strong suit.”

“Well,” Cas says, reaching for Dean’s hand and planting a kiss on his knuckles. “I’ve got a filling missing from one of my back teeth.” He grins up at Dean and whispers, into the ever-dwindling space between them, “Nobody’s perfect.”

Dean pulls him in, and Cas lets himself be kissed.

***

_ Chicago Tribune (Late Edition), April 7, 1929 _

**_Novaks Rich Again — Engagement Announced!_ **

_ The fortunes of the Novak family, made infamous by industrialist Charles Novak’s fall from grace, have seen a dramatic reversal. _

_ Following Charles Novak’s disappearance last summer, the Novak assets were frozen, leaving sons Gabriel and Castiel Novak in dire poverty. _

_ Now, things are looking up for the Novaks, as President Hoover himself has pardoned Charles Novak in absentia, leaving all his assets to become available to his family once more. _

_ Anonymous sources tell us the pardon was issued at the direct request of the Knight family of Texas, proprietors of Knight Oil and Flammables. _

_ This version of events would seem to be confirmed by the recently announced engagement between Gabriel Novak and Josephine Knight, heiress to the Knight fortune. A merger between Novak Industries and Knight Oil has also been rumored. _

_ Reached at the Novak mansion by a reporter, Gabriel Novak seemed in a joking mood, saying, “I plan to live large on my wife’s money and leave the running of the business up to her.” _

_ Less is known about the future plans of younger brother Castiel Novak, though it’s rumored he will soon open a nightclub in Palm Beach, Florida, with an unnamed business partner. _

**END PART II**

*** 

**Epilogue**

_ 1934: The Great Depression _

At twenty minutes to midnight, traffic is lively on the streets of Palm Beach, crowded hotel shuttles and open-topped coupes filled with revelers competing for space along the oceanfront boulevard.

Out there, in the rest of the country, it’s a time of tent cities and breadlines, hunger and despair. But in Florida’s resort towns, the party goes on for those who can afford it — especially now that Prohibition has met its long overdue demise.

Beside the busy boulevard, in the center of town, sits a sprawling, Spanish mission-style building. Atop its roof is a red neon sign that reads “Surprise!” in looping script. It crackles on and off with a cheerful buzz.

Visitors looking for a good time pass below that neon beacon and through a pair of glass doors, past the brass sign that reads, “C. Novak and D. Winchester, Proprietors.” The doors open onto a clubroom that’s crowded with richly dressed dancers. The intricately textured wallpaper gleams emerald in the soft light of the wall sconces. Overhead, a vaulted ceiling soars, painted with a mural of fierce angelic warriors whose blades are poised above grimacing demons.

A long bar takes up one side of the room, with a mirror behind it. The glass reflects back the writhing mass of bodies, swaying in time to the fast-paced tune offered up by the band on stage.

On certain special nights, the proprietors themselves perform on that stage, on bass fiddle and vocals, respectively. Whenever this happens, it's a big draw for tourists and locals alike. People mostly want to see Castiel Novak for his famous name — “he’s the younger brother of Gabriel Novak, you know, who’s married to Josephine Knight?” they’ll say in hushed tones. But Dean Winchester is famous for his stage presence and charisma, and his willingness to work the room after a performance.

Many of the other performers are popular in town as well: there’s Dapper Donna, known for her cross-dressing act and deep, booming alto; Charlie Bradbury, the red-haired trombonist; and Dorothy Baum, who plays the clarinet like she was born to it.

But still, none of them fascinate the way the club’s co-owners do. Locals like to drive their visiting friends past the luxurious beachside mansion the two of them share, presumably for the convenience of discussing club business at all hours of the day and night.

Indeed, Surprise! is an unusual club in some ways. Not where its front room is concerned, of course, but its back door is another matter entirely.

At most hours of the day or night, a person in need who knocks on that door will be ushered inside, usually by a cheerful woman named Mary. Rumor has it she’ll serve anyone a warm meal, with a smile and a whispered, “My son’s chef cooked this, not me, so don’t you worry.”

You might think a nightclub that runs its own soup kitchen is sufficiently unusual, but there’s more still. Tucked away in a corner of the clubroom, hidden behind a heavy blue curtain, is a door marked “Staff Only.” 

Behind this door lies the club’s inner sanctum, where only a lucky few are ever permitted to enter. Those who do enter follow the sound of laughter to a series of smaller rooms, where music is played on gramophones, jokes are told, and men and women alike keep whatever company they please.

In fact, the proprietors of Surprise! can often be found in these exclusive environs, sharing a drink with friends. But on the particular night our story ends, they have retreated to a private room, curled up in the corner of a chaise longue.

“You know,” Dean says, tightening his arms around Cas, “we’ve got a pretty good thing going here.”

Cas hums his agreement and melts further into Dean’s chest. 

“Could be better though,” Dean says thoughtfully.

Cas raises his head to squint up at Dean. “Oh?”

“You remember those pictures Gabe showed us last time he came to visit? The French ones?” A small blush spreads across Dean’s cheeks. 

“The  _ bondage _ and  _ fetish _ ones?” Cas asks, emphasizing each word with gusto. Dean’s blush deepens.

“Yeah. Those ones.” Dean clears his throat. “I was thinking we could… you know, add a private room to the club, with some… amenities.”

Cas rests his forehead against Dean’s sternum, chuckling. “Dean, if you’re uncomfortable even talking about these things, I’m not sure — ”

“I’m not uncomfortable. The opposite actually,” Dean says, shifting a little to demonstrate the obvious truth of that statement. 

In response, Cas does some shifting of his own, pulling a low moan up Dean’s throat. 

“You remember the picture of the women’s underwear with the slit down the rear?” Cas asks.

Dean nods, watching avidly as Cas rolls onto his side so he can trail his fingers slowly along the waistband of Dean’s trousers. Cas quirks a small smile when he hears the hitch in Dean’s breath.

“Do you think,” Cas whispers in Dean’s ear as his fingers travel further south, “I might persuade you to wear something like that?”

“I wouldn’t be surprised,” Dean croaks. 

“Well, who knew?” Cas says as he undoes the buckle of Dean’s belt. “I guess some people _ are _ perfect.”

**Notes for the Chapter:**

> The pictures Dean and Cas discuss in the epilogue [are here](https://dangerousminds.net/comments/fierce_vintage_fetish_wear_from_the_1920s_and_1930s) (warning for NSFW content). 
> 
> Again, thank you so much to everyone who has commented or given kudos on this story. You're the reason I keep writing! If you enjoyed this story, consider [giving it a reblog](https://friendofcarlotta.tumblr.com/post/637867522185723904/nobodys-perfect-now-complete-read-it-on-ao3) on tumblr?
> 
> If you want to follow along with my next fic, you can [subscribe to me](https://archiveofourown.org/users/FriendofCarlotta/pseuds/FriendofCarlotta) on my author page or [follow me on tumblr](https://friendofcarlotta.tumblr.com).
> 
> I'm currently co-writing an epic finale fix-it that, with any luck, should start posting in the near future. I hope to see you there!

**Author's Note:**

> Comments are life!! If you enjoyed this, please leave me one, or hit that kudos button. I appreciate your feedback more than I can say.
> 
> If you think you might want to read more of my writing in the future, you can [subscribe to me](https://archiveofourown.org/users/FriendofCarlotta) on my author page!
> 
> Come yell at me on [tumblr](https://friendofcarlotta.tumblr.com)!


End file.
